Contemporary Aspects of Boron: Chemistry and Biological Applications (eBook)

Cover 1
Table of Contents 10
Chapter 1: Chemistry of the diboron compounds 14
Introduction 15
Preparation of Diboron Compounds and their Properties 16
Reactions of Diboron Compounds 29
References 65
Chapter 2: Recent developments in bisdiborane chemistry: B-C-B, B-C-C-B, B-C=C-B, and B-C=C-B compounds and their biological applications 72
Introduction 73
Formation of B-C-B Compounds 74
Geminal Organoboron Compounds 81
Formation, Reactivity and Biological Activity of B-C-C-B, B-C=C-B, and B-C=C-B Compounds 98
References 126
Chapter 3: Applied Suzuki cross-coupling reaction for syntheses of biologically active compounds 132
Introduction 133
Synthesis of Biologically Active Compounds via Cross Coupling Reaction Catalyzed by Palladium 133
Cross-coupling of Alkynylborane Derivatives with Haloarenes 146
Cross-coupling of Alkynylborane Derivatives 168
Cross-coupling of Alkylborane Derivatives 179
Synthesis of Macrocycles 197
Modification of Nucleosides using Suzuki-Miyaura Coupling 235
Synthesis of Substituted Porphyrins 249
Additional Application of the Suzuki Cross-coupling Reaction 254
Synthesis of Macrocyclic Compounds 256
Synthesis of Tetracyclic Systems 263
Synthesis of Polycyclic Ethers 274
Synthesis of Disubstituted Furans 280
Synthesis of GeranylGeranyl Diphosphate Derivatives 283
Synthesis of Spiroquinolizidine Derivatives 284
Synthesis of Carbohydrate-Substituted Phosphines 286
Synthesis of Novel Thyroid Hormone Analogues: 5'-Aryl Substituted GC-1 Derivatives 293
References 295
Chapter 4: Synthesis of selected biologically active compounds via allylboration 312
Introduction 313
Synthesis of Heterocyclic Compounds 314
Synthesis of N-Lactone Rings 332
Allylboration of Nitrogen Heterocycles 339
References 344
Chapter 5: Boron neutron capture therapy. 350
Introduction 351
The Concept of Boron Neutron Capture Therapy 351
BNCT in the Treatment of Cancer 354
Boron Targeting to Cancer Tissues 357
Summary 373
References 374
Chapter 6: Boron enolates in the syntheses of natural products 380
Introduction 382
Synthesis of the Anti-Cancer Marine Natural Product (+)-Discodermolide 382
Enantioselective Total Synthesis of (+)-Leucascandrolide- A Macrolactone 383
Synthesis of the C29-C51 Subunit of Altohyrtin C (Spongistatin 2) 384
Asymmetric Synthesis of the Polyene Macrolide Antibiotic RK-397 385
Asymmetric Total Synthesis of Spongistatins 1 and 2 385
Synthesis of the Microtubule-Stabilizing Agent (-)-Laulimalide 386
Synthesis of (2S,3S)-and (2R,3R)-Beta-Hydroxyornithine 387
Synthesis of Concanamycin F 387
Synthesis of an Isomer of Membrenone C 388
Synthesis of Doliculide 389
Synthesis of Tri- and Tetrapeptide S: the Extended C-Terminus of Bleomycin A2 389
Synthesis of A (9S)-Macrolide Intermediate for Oleandomycin 390
Synthetic Studies on Antitumor Antibiotic Bleomycin 390
Synthesis of the Esterase Inhibitor (±)- Ebelactone A 391
Synthesis of the Oviposition-Deterring Pheromone in Rhagoletis cerasi 391
Synthesis of (±)-Hernandulcin 392
Synthesis of Beta-Lactam Antibiotics 392
Synthesis of (+)-Pseudomonic Acid C 393
Synthesis of Masamune Norephedrine Esters 394
Synthesis of L-Daunosamine and D-Ristosamine Derivatives 394
SEMI- Synthesis of Taxol 395
Synthesis of the Pyrrolizidine Ring System 395
Synthesis of (-)-Branched Unusual Amino Acids 396
Synthesis of Alpha-Amino Acids 396
Synthesis of 1 -Beta-Methylcarbapenem Antibiotics 397
Synthesis of Nakadomarin 398
Synthesis of 11-Beta,17-Beta-Diaryl-18A-Homo-19-Norsteroids 398
Synthesis of the Central C18-C30 Core of the Phorboxazole 399
Synthesis of A C17-C32 Subunit of Scytophycin C 399
Synthesis of the Archaebacterial C40 Diol 400
Synthesis of Anthracycline Glycosides 400
References 401
Chapter 7: Boronated saccharides: potential applications 404
Introduction 406
Boronic Acids-Saccharide Interaction the Basics
Chemosensing 409
Transport 447
Boron and Plants 459
Chromatography 464
Boron and Diabetes 474
Boron and Cancer 478
Drug Delivery 483
Miscellaneous Biological Applications of Boron Saccharide Interactions 485
References 492
Chapter 8: a-Aminoboronic acids, amine cyanoboranes, amine carboxyboranes and their derivatives 508
Introduction 509
Alpha-Aminoboronic Acids 509
Amine Cyanoboranes and Amine Carboxyboranes 535
Biological Activities of Amine Cyano- and Carboxyboranes and their Derivatives 550
References 557
Chapter 9: Environmental aspects of boron 564
Introduction 565
Boron Chemistry 566
Boron in Soils 573
Boron in Plants 575
Water Desalination 593
References 606
Index 612