Boronic acids: preparation and application in organic synthesis and medicine (Weinheim, 2005). - ОГЛАВЛЕНИЕ / CONTENTS
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ОбложкаBoronic acids: preparation and application in organic synthesis and medicine / ed. by Hall D.G. - Weinheim: Wiley-VCH, 2005. - 549 p. - ISBN 978-3-527-30991-7
 

Оглавление / Contents
 
    Preface .................................................... XV

    List of Authors ........................................... XIX

    List of Abbreviations ..................................... XXI

1   Structure, Properties, and Preparation Of Boronic Acid
    Derivatives. Overview of Their Reactions and Applications ... 1
    D.G. Hall

1.1 Introduction ................................................ 1
1.2 Structure and Properties of Boronic Acid Derivatives ........ 2
    1.2.1 General Types and Nomenclature of Boronic Acid
          Derivatives ........................................... 2
    1.2.2 Boronic Acids ......................................... 3
          1.2.2.1 Structure and Bonding ......................... 3
          1.2.2.2 Physical Properties and Handling .............. 7
          1.2.2.3 Safety Considerations ......................... 8
          1.2.2.4 Acidic Character .............................. 8
          1.2.2.5 Chemical Stability ........................... 13
    1.2.3 Boronic Acid Derivatives ............................. 14
          1.2.3.1 Boroxines .................................... 14
          1.2.3.2 Boronic Esters ............................... 15
          1.2.3.3 Dialkoxyboranes and other Heterocyclic
                  Boranes ...................................... 23
          1.2.3.4 Diboronyl Esters ............................. 24
          1.2.3.5 Azaborolidines and other Boron
                  Heterocycles ................................. 24
          1.2.3.6 Dihaloboranes and Monoalkylboranes ........... 26
          1.2.3.7 Trifluoroborate Salts ........................ 27
1.3 Synthesis of Boronic Acids and their Esters ................ 28
    1.3.1 Arylboronic Acids .................................... 28
          1.3.1.1 Electrophilic Trapping of Arylmetal
                  Intermediates with Borates ................... 28
          1.3.1.2 Transmetallation of Aryl Silanes and
                  Stannanes .................................... 34
          1.3.1.3 Coupling of Aryl Halides with Diboronyl
                  Reagents ..................................... 35
          1.3.1.4 Direct Boronylation by Transition Metal-
                  catalyzed Aromatic C-H Functionalization ..... 35
          1.3.1.5 Other Methods ................................ 36
    1.3.2 Diboronic Acids ...................................... 36
    1.3.3 Heterocyclic Boronic Acids ........................... 37
    1.3.4 Alkenylboronic Acids ................................. 37
          1.3.4.1 Electrophilic Trapping of Alkenymetal
                  Intermediates with Borates ................... 37
          1.3.4.2 Transmetallation Methods ..................... 37
          1.3.4.3 Transition-metal Catalyzed Coupling between
                  Alkenyl Halides/Triflates and Diboronyl
                  Reagents ..................................... 42
          1.3.4.4 Hydroboration of Alkynes ..................... 43
          1.3.4.5 Alkene Metathesis ............................ 46
          1.3.4.6 Other Methods ................................ 46
    1.3.5 Alkynylboronic Acids ................................. 48
    1.3.6 Alkylboronic Acids ................................... 48
    1.3.7 Allylic Boronic Acids ................................ 49
    1.3.8 Chemoselective Transformations of Compounds
          containing a Boronic Acid (Ester) Substituent ........ 49
          1.3.8.1 Oxidative Methods ............................ 50
          1.3.8.2 Reductive Methods ............................ 51
          1.3.8.3 Generation and Reactions of α-Boronyl-
                  substituted Carbanions and Radicals .......... 51
          1.3.8.4 Reactions of (α-Haloalkyl)boronic Esters ..... 54
          1.3.8.5 Other Transformations ........................ 55
1.4 Isolation and Characterization ............................. 57
    1.4.1 Chromatography and Recrystallization ................. 57
    1.4.2 Solid Supports for Boronic Acid Immobilization and
          Purification ......................................... 58
          1.4.2.1 Diethanolaminomethyl Polystyrene ............. 59
          1.4.2.2 Other Solid-supported Diol Resins ............ 60
          1.4.2.3 Soluble Diol Approaches ...................... 60
    1.4.3 Analytical and Spectroscopic Methods for Boronic
          Acid Derivatives ..................................... 61
          1.4.3.1 Melting Points and Combustion Analysis ....... 61
          1.4.3.2 Mass Spectrometry ............................ 61
          1.4.3.3 Nuclear Magnetic Resonance Spectroscopy ...... 61
          1.4.3.4 Other Spectroscopic Methods .................. 62
1.5 Overview of the Reactions of Boronic Acid Derivatives ...... 62
    1.5.1 Metallation and Metal-catalyzed Protodeboronation .... 62
    1.5.2 Oxidative Replacement of Boron ....................... 63
          1.5.2.1 Oxygenation .................................. 63
          1.5.2.2 Amination .................................... 65
          1.5.2.3 Halogenation ................................. 66
    1.5.3 Carbon-Carbon Bond forming Processes ................. 68
          1.5.3.1 Palladium-catalyzed Cross-coupling with
                 Carbon Halides (Suzuki Coupling) .............. 69
          1.5.3.2 Allylation of Carbonyl Compounds ............. 71
          1.5.3.3 Uncatalyzed Additions to Imines and
                  Iminiums ..................................... 73
          1.5.3.4 Rhodium-catalyzed Additions to Aldehydes
                  and Alkenes .................................. 73
          1.5.3.5 Heck-type Coupling to Alkenes and Alkynes .... 73
    1.5.4 Carbon-Heteroatom Bond forming Processes ............. 73
          1.5.4.1 Copper-catalyzed Coupling with Nucleophilic
                  Oxygen and Nitrogen-containing Compounds ..... 73
    1.5.5 Other Reactions ...................................... 74
1.6 Overview of other Applications of Boronic Acid
    Derivatives ................................................ 76
    1.6.1 Use as Reaction Promoters and Catalysts .............. 76
    1.6.2 Use as Protecting Groups for Diols and Diamines ...... 78
    1.6.3 Use as Supports for Derivatization and Affinity
          Purification of Diols, Sugars, and Glycosylated
          Proteins ............................................. 79
    1.6.4 Use as Receptors and Sensors for Carbohydrates and
          other Small Molecules ................................ 81
    1.6.5 Use as Antimicrobial Agents and Enzyme Inhibitors .... 81
    1.6.6 Use in Neutron Capture Therapy for Cancer ............ 82
    1.6.7 Use in Transmembrane Transport ....................... 83
    1.6.8 Use in Bioconjugation and Labeling of Proteins and
          Cell Surface ......................................... 84
1.7 References ................................................. 85

2   Metal-catalyzed Borylation of Alkanes and Arenes via C-H
    Activation for Synthesis of Boronic Esters ................ 101
    T. Ishiyama and N. Miyaura
2.1 Introduction .............................................. 101
2.2 Borylation of Aromatic Halides and Triflates .............. 102
    2.2.1 Cross-coupling Reaction of Diborons ................. 102
    2.2.2 Cross-coupling Reaction of Pinacolborane ............ 104
2.3 Aliphatic C-H Borylation .................................. 105
    2.3.1 Rhenium-catalyzed Photochemical Reaction ............ 106
    2.3.2 Rhodium-catalyzed Reaction .......................... 107
2.4 Aromatic C-H Borylation ................................... 109
    2.4.1 Rhenium-catalyzed Photochemical Reaction ............ 109
    2.4.2 Rhodium-catalyzed Reactions ......................... 109
    2.4.3 Iridium-catalyzed Reactions ......................... 110
    2.4.4 Catalytic Cycle ..................................... 116
2.5 Benzylic C-H Borylation ................................... 118
    Acknowledgments ........................................... 119
2.6 References ................................................ 119

3   Coupling Reactions of Areneboronic Acids or Esters with
    Aromatic Electrophiles .................................... 123
    A. Suzuki
3.1 Introduction .............................................. 123
3.2 Coupling Reactions of Areneboronic Acid Derivatives ....... 124
    3.2.1 With Aryl Halides. Synthesis of Biaryls ............. 124
          3.2.1.1 Aromatic-Aromatic Coupling .................. 124
          3.2.1.2 Aromatic-Heteroaromatic and
                  Heteroaromatic-Heteroaromatic Couplings ..... 131
          3.2.1.3 Coupling of Sterically Hindered
                  Arylboronic Acids or ones Possessing
                  Electron-attracting Substituents ............ 141
          3.2.1.4 Modified Catalysts and Ligands .............. 144
          3.2.1.5 Solid-phase Synthesis (Combinatorial
                  Methodology) ................................ 153
    3.2.2 With Other Organic Halides, including Aryl
          Chlorides and Electrophiles ......................... 156
    3.2.3 Miscellaneous ....................................... 160
3.3 Conclusion ................................................ 166
3.4 References ................................................ 167

4   Rhodium-catalyzed Additions of Boronic Acids to Alkenes
    and Carbonyl Compounds .................................... 171
    K. Yoshida and T. Hayashi
4.1 Introduction .............................................. 172
4.2 Addition of Organoboronic Acids to α, β-Unsaturated
    Ketones ................................................... 172
4.3 Mechanism ................................................. 176
4.4 Addition of Organoboronic Acids to Other Alkenes .......... 181
4.5 Addition of Organoboronic Acids to Alkynes ................ 192
4.6 Addition of Organoboronic Acids to Aldehydes and Imines ... 195
4.7 Addition of Organoboronic Acids to Anhydrides ............. 200
4.8 Outlook ................................................... 201
4.9 References ................................................ 202

5    Recent Advances in Copper-promoted C-Heteroatom Bond
     Cross-coupling Reactions with Boronic Acids and
     Derivatives .............................................. 205
     D.M.T. Chan and P.Y.S. Lam
5.1  General Introduction ..................................... 205
5.2  Copper-mediated Boronic Acid C-O and C-N Cross-
     coupling - Historical Background ......................... 206
5.3  C(aryl)-O Cross-coupling ................................. 207
     5.3.1 Intermolecular C-O Cross-coupling .................. 207
     5.3.2 Intramolecular C-O Cross-coupling .................. 210
5.4  C-N Cross-coupling ....................................... 212
     5.4.1 C-N (Non-heteroarene NH) Cross-coupling ............ 212
           5.4.1.1 Application in Solid-phase Synthesis ....... 214
     5.4.2 C-N (Heteroarene) Cross-coupling ................... 215
           5.4.2.1 Factor Xa Inhibitors ....................... 217
           5.4.2.2 Purines .................................... 229
           5.4.2.3 Heteroarene-Heteroarene Cross-coupling ..... 220
5.5  C-O vs. C-N Cross-couplings .............................. 221
5.6  C-N and C-O Cross-coupling with Alkenylboronic Acids ..... 222
5.7  C-S Cross-coupling ....................................... 224
5.8  C-N and C-O Cross-coupling with Boronic Acid
     Derivatives .............................................. 224
     5.8.1 Boroxines, Boronic Esters and Trifluoroborate
           Salts .............................................. 224
     5.8.2 Alkylboronic Acids ................................. 227
5.9  Mechanistic Considerations ............................... 227
     5.9.1 Electronic Effects ................................. 227
     5.9.2 Solvent Effects .................................... 228
     5.9.3 Ligand or Base Effects ............................. 229
     5.9.4 Mechanism .......................................... 230
     5.9.5 Side-products ...................................... 231
5.10 Other Organometalloids ................................... 233
5.11 Conclusion ............................................... 233
5.12 Appendix ................................................. 235
5.13 References ............................................... 238

6   Recent Advances in the Preparation of Allylboronates and
    Their Use in Tandem Reactions with Carbonyl Compounds ..... 241
    J.W.J. Kennedy and D.G. Hall
6.1 Introduction .............................................. 241
6.2 Preparation of Allylboronates ............................. 243
    6.2.1 Direct Methods ...................................... 243
          6.2.1.1 Allylboronates from Allylmetal
                  Intermediates ............................... 243
          6.2.1.2 Allylboronates from Alkenylmetal
                  Intermediates ............................... 244
          6.2.1.3 Allylboronates from the Hydroboration of
                  1,3-Butadienes and Allenes .................. 246
          6.2.1.4 Allylboronates from the Transition-metal
                  Catalyzed Diboration and Silaboration of
                  Dienes and Allenes .......................... 247
          6.2.1.5 Allylboronates from Palladium-catalyzed
                  Cross-coupling Reactions with Alkenyl
                  Fragments ................................... 249
          6.2.1.6 Allylboronates from Palladium-catalyzed
                  Cross-coupling Reactions with Allyl
                  Electrophiles ............................... 249
    6.2.2 Indirect Methods .................................... 250
          6.2.2.1 Allylboronates from Alcoholysis of
                  Triallylboranes ............................. 250
          6.2.2.2 Allylboronates from Homologation of
                  Alkenylboronates ............................ 250
          6.2.2.3 Allylboronates from Allylic Rearrangement
                  of Alkenylboronates ......................... 251
          6.2.2.4 Allylboronates from Isomerization of
                  Alkenylboronates ............................ 252
          6.2.2.5 Allylboronates by Cycloadditions of
                  Dienylboronates ............................. 253
          6.2.2.6 Allylboronates by Olefin Metathesis ......... 254
6.3 Reactions of Allylboronates ............................... 256
    6.3.1 Additions to Aldehydes - Formation of Homoallylic
          Alcohols ............................................ 256
          6.3.1.1 Stereoselectivity and Mechanism of
                  Non-catalyzed Additions ..................... 256
          6.3.1.2 Lewis Acid-catalyzed Additions .............. 257
          6.3.1.3 Stereoselective Additions with Chiral
                  Allylboronates .............................. 259
    6.3.2 Additions to Ketones ................................ 263
    6.3.3 Additions to Imine Derivatives ...................... 264
6.4 Applications of Allylboronates in Tandem Reactions with
    Carbonyl Compounds ........................................ 266
    6.4.1 Allylboration as the Terminal Process ............... 266
          6.4.1.1 Tandem [4+2] Cycloaddition/Allylation ....... 266
          6.4.1.2 Tandem Hydroformylation/Intramolecular
                  Allylation .................................. 267
          6.4.1.3 Tandem Alkene Cross-metathesis/Allylation ... 268
          6.4.1.4 Tandem Diene Hydroboration/Allylation ....... 269
          6.4.1.5 Tandem Diene Diborylation (Silaboration)/
                  Allylboration ............................... 270
          6.4.1.6 Tandem Allylic Borylation/Intramolecular
                  Allylation .................................. 271
    6.4.2 Allylboration as the Initiating Process ............. 271
          6.4.2.1 Tandem Allylation/Allylation ................ 271
          6.4.2.2 Tandem Allylation/Lactonization ............. 272
          6.4.2.3 Tandem Allylation/Dioxene Thermolysis ....... 273
6.5 Conclusion ................................................ 274
6.6 References ................................................ 274

7   Nucleophilic Addition Reactions of Aryl and
    Alkenylboronic Acids and Their Derivatives to Imines and
    Iminium Ions .............................................. 279
    R.A. Batey
7.1 Introduction .............................................. 279
7.2 Petasis Borono-Mannich Reaction: Iminium Ions Lacking
    Neighboring Heteroatom Functionality ...................... 282
    7.2.1 Discovery of the Reaction using Paraformaldehyde .... 281
    7.2.2 Reactions of Iminium Ions Derived from Simple
          Aldehydes ........................................... 281
7.3 Practicality, Scope and Reaction Mechanism ................ 282
    7.3.1 Synthetic Benefits of the Petasis Borono-Mannich
          Reaction ............................................ 282
    7.3.2 Mechanistic Observations ............................ 283
    7.3.3 Substrate Scope and the Effect of Neighboring
          Heteroatoms ......................................... 284
7.4 Petasis Borono-Mannich Reaction: Iminium Ions Possessing
    Neighboring Heteroatom Functionality ...................... 285
    7.4.1 Reactions of Glyoxylic Acid-derived Iminium Ions .... 285
          7.4.1.1 Diastereoselective Addition Reactions to
                  Iminium Ions Derived from Chiral Amines
                  and Glyoxylic Acid .......................... 289
          7.4.1.2 Enantioselective Addition Reactions to
                  Glyoxylic Acid-derived Iminium Ions using
                  Chiral Boronic Esters ....................... 289
    7.4.2 Reactions of Iminium Ions Bearing α-Heteroatom
          Substituents ........................................ 290
          7.4.2.1 Diastereoselective Addition Reactions ....... 290
    7.4.3 Reactions of Iminium Ions Bearing β-Heteroatom
          Substituents ........................................ 291
    7.4.4 Addition Reactions using Iminium Ions Derived from
          Hydrazines, Hydroxylamines and Sulfinamides ......... 293
7.5 Polymer-supported Petasis Borono-Mannich Reactions ........ 294
7.6 Other Types of Addition Reactions ......................... 297
    7.6.1 Lewis Acid Promoted Additions: Addition Reactions
          to N-Acyliminium Ions ............................... 297
    7.6.2 Lewis Acid Promoted Additions of
          Organotrifluoroborate Salts ......................... 298
    7.6.3 Rhodium-catalyzed Additions of Boronic Acids to
          N-Sulfonylimines .................................... 299
    7.6.4 Dialkylzinc-promoted Additions of Alkenylboronic
          Esters to Nitrones .................................. 301
    7.6.5 Nickel-catalyzed Couplings of Boronic Acids with
          Alkynes and Imines .................................. 301
7.7 Concluding Remarks ........................................ 302
7.8 References ................................................ 303

8   (α-Haloalkyl)boronic Esters in Asymmetric Synthesis ....... 305
    D.S. Matteson
8.1 Introduction .............................................. 305
8.2 General Description of (α-Haloalkyl)boronic Ester
    Chemistry ................................................. 305
    8.2.1 A Brief History of Boronic Ester Chemistry .......... 305
    8.2.2 C2-symmetrical Boronic Esters ....................... 306
8.3 Boronic Ester Intermediates in Synthesis .................. 311
    8.3.1 Boronic Ester Intermediates without Functional
          Substituents ........................................ 311
    8.3.2 Halogen-substituted Boronic Esters .................. 315
    8.3.3 Alkoxy-substituted Boronic Esters ................... 316
    8.3.4 Carbonyl Substituents ............................... 323
    8.3.5 Nitrile Substituents ................................ 325
    8.3.6 Amino and Amido Substituents ........................ 328
    8.3.7 Azido Substituents .................................. 331
    8.3.8 Other Applications of (α-Haloalkyl)boronic Esters ... 333
8.4 Other Aspects of (α-Chloroalkyl)boronic Ester Chemistry ... 334
    8.4.1 Replacement of Boronic Ester Groups ................. 334
    8.4.2 Chain Extension with (Dialkoxymethyl)lithium ........ 336
    8.4.3 (α-Iodoalkyl)boronic Esters via (Phenylthiomethyl)
          boronic Esters ...................................... 336
    8.4.4 Free Radicals from (α-Haloalkyl)boronic Esters ...... 337
    8.4.5 Metal Substitutions of (α-Haloalkyl)boronic
          Esters .............................................. 338
8.5 Conclusion ................................................ 340
8.6 References ................................................ 340

9   Cycloadditions and Other Additions to Alkenyl-, Alkynyl-
    and Dienyl Boronic Esters ................................. 343
    B. Carboni and F. Carreaux
9.1 Ionic Addition ............................................ 343
    9.1.1 Halogenation and Hydrohalogenation .................. 343
    9.1.2 Addition of Organometallics ......................... 345
9.2 Radical Additions ......................................... 347
9.3 Cycloaddition Reactions ................................... 350
    9.3.1 Cyclopropanation .................................... 350
    9.3.2 Diels-Alder Reactions ............................... 351
          9.3.2.1 Alkenylboronates as Dienophiles ............. 351
          9.3.2.2 Alkynylboronates as Dienophiles ............. 355
          9.3.2.3 1,3-Dienyl-1-boronates as Dienes ............ 356
          9.3.2.4 1,3-Dienyl-1-boronates as Heterodienes ...... 360
          9.3.2.5 1,3-Dienyl-2-boronates as Dienes ............ 361
    9.3.3 1,3-Dipolar Cycloadditions .......................... 363
          9.3.3.1 Diazoalkanes ................................ 363
          9.3.3.2 Nitrile Oxides .............................. 364
          9.3.3.3 Nitrones .................................... 365
          9.3.3.4 Azomethyne Ylides ........................... 366
    9.3.4 Other Cycloadditions ................................ 367
9.4 Metathesis Reactions ...................................... 368
9.5 Miscellaneous Reactions ................................... 370
9.6 Conclusions ............................................... 372
9.7 References ................................................ 373

10   Organoboronic Acids and Organoborinic Acids as
     Brønsted-Lewis Acid Catalysts in Organic Synthesis ....... 377
     K. Ishihara
10.1 Introduction ............................................. 377
10.2 Diarylborinic Acids ...................................... 377
10.3 Arylboronic Acids ........................................ 381
10.4 Chiral Boronate Lewis Acids .............................. 389
     10.4.1 Enantioselective Carbo Diels-Alder Reactions ...... 389
     10.4.2 Enantioselective Hetero-Diels-Alder Reactions ..... 399
     10.4.3 Enantioselective Mukaiyama Aldol Reactions ........ 400
     10.4.4 Enantioselective Sakurai-Hosomi Allylation
            Reactions ......................................... 405
     10.4.5 Enantioselective Reduction ........................ 406
     10.4.6 Enantioselective Cyclopropanation ................. 407
10.5 Conclusions .............................................. 407
10.6 References ............................................... 408

11   Oxazaborolidines as Asymmetric Inducers for
     the Reduction of Ketones and Ketimines ................... 411
     B.T. Cho
11.1 Introduction ............................................. 411
11.2 Oxazaborolidines ......................................... 413
11.3 Oxazaborolidine-catalyzed Asymmetric Reduction of
     Ketones .................................................. 414
     11.3.1 Mechanism of OAB-catalyzed Ketone Reduction ....... 415
     11.3.2 Unfunctionalized Acyclic and Aryl Alkyl Ketones ... 416
     11.3.3 Diaryl Ketones .................................... 416
     11.3.4 Heterocyclic Ketones .............................. 417
     11.3.5 Functionalized Ketones ............................ 418
            11.3.5.1 α-Halo and α-Sulfonyloxy Ketones ......... 418
            11.3.5.2 α-Hydroxy Ketones and Diketones .......... 421
            11.3.5.3 α-Keto Acetals and Thioketals ............ 422
            11.3.5.4 Keto Esters and meso-Imides .............. 423
            11.3.5.5 α, β-Enones and Ynones ................... 424
            11.3.5.6 α-Azido and Imino Ketones ................ 426
            11.3.5.7 α-, β- and γ-Keto Phosphates ............. 427
            11.3.5.8 β-Keto Sulfides and Sulfones ............. 428
     11.3.6 Atropo-enantioselective Reduction ................. 429
     11.3.7 Kinetic Resolution of Racemic Ketones and Biaryl
            Lactones .......................................... 429
11.4 Asymmetric Reduction of Prochiral Ketimines .............. 430
     11.4.1 Ketoxime Derivatives .............................. 430
     11.4.2 N-Substituted Ketimines ........................... 433
11.5 Summary and Conclusions .................................. 434
     Acknowledgments .......................................... 436
11.6 References ............................................... 436

12   Boronic Acid-based Receptors and Sensors for
     Saccharides .............................................. 441
     T.D. James
12.1 Introduction ............................................. 441
12.2 Fluorescence ............................................. 445
     12.2.1 Internal Charge Transfer (ICT) .................... 445
     12.2.2 Photoinduced Electron Transfer (PET) .............. 448
     12.2.3 Other Fluorescent Sensors ......................... 458
12.3 Colorimetric Sensors ..................................... 461
12.4 Electrochemical Sensors .................................. 467
12.5 Assay Systems ............................................ 468
12.6 Polymer and Surface Bound Sensors ........................ 471
12.7 Conclusions .............................................. 474
12.8 References ............................................... 475

13   Biological and Medicinal Applications of Boronic Acids ... 481
     W. Yang, X. Gao, and B. Wang
13.1 Introduction ............................................. 481
13.2 Boronic Acid Compounds as Enzyme Inhibitors .............. 484
     13.2.1 Protease Inhibitors that Bind to One Side of
            the Active Site ................................... 485
     13.2.2 Boronic acid-Nucleophile Complex Formed in
            the Enzyme Active Site as a way to Improve
            Potency and Selectivity ........................... 488
     13.2.3 Boronic Acids used for the Binding of the Non-
            scissile Position ................................. 490
     13.2.4 Boronic Esters as Enzyme Inhibitors ............... 493
     13.2.5 Boronic Acids as Inhibitors of Glycosidases ....... 493
     13.2.6 Boronic Acids as Agents Targeting the Human
            Immunodeficiency Virus ............................ 494
     13.2.7 Bortezomib as a Proteasome Inhibitor for Cancer
            Therapy: A Successful Example ..................... 494
     13.2.8 Others ............................................ 496
13.3 Boronic Acid Compounds as Boron Neutron Capture Therapy
     (BNCT) Agents ............................................ 499
13.4 Boronic Acid Compounds as Drug (Insulin) Delivery
     Devices and for In Vivo Glucose Imaging .................. 500
13.5 Cell Surface Carbohydrate Recognition by Artificial
     Lectins-Boronolectins .................................... 503
13.6 Conclusions .............................................. 506
     Acknowledgments .......................................... 506
13.7 References ............................................... 507


 
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