Heterocycles in natural product synthesis

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Weitere Verfasser: Majumdar, Krishna Chandra 1945- (HerausgeberIn), Chattopadhyay, Shital K. (HerausgeberIn)
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Veröffentlicht: Weinheim Wiley-VCH-Verl. 2011
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adam_text IMAGE 1 CONTENTS PREFACE XV LIST OF CONTRIBUTORS XVII PART ONE STRAINED HETEROCYCLES IN THE SYNTHESIS OF NATURAL PRODUCTS 1 1 AZIRIDINES IN NATURAL PRODUCT SYNTHESIS 3 CANDICE BOTUHA, FABRICE CHEMLA, FRANCK FERREIRA AND ALEJANDRO PEREZ-LUNA 1.1 INTRODUCTION 3 1.2 SYNTHESIS OF NATURAL PRODUCTS CONTAINING AZIRIDINE UNITS 3 1.2.1 SYNTHESIS OF AZIRIDINE-2,3-DICARBOXYLIC ACID 3 1.2.2 SYNTHESIS OF (Z)-DYSIDAZIRINE 5 1.2.3 SYNTHESES OF MITOMYCINS 5 1.2.4 SYNTHESES OF FR-900482 AND FR-66979 8 1.3 SYNTHESIS OF NATURAL PRODUCTS INVOLVING THE TRANSFORMATION OF AN AZIRIDINE MOIETY 10 1.3.1 NUDEOPHILIC RING-OPENING OF AZIRIDINES FOR NATURAL PRODUCT SYNTHESIS 10 1.3.1.1 CARBON-CENTERED NUDEOPHILES 11 1.3.1.2 NITROGEN-CENTERED NUCLEOPHILES 15 1.3.1.3 OXYGEN-CENTERED NUCLEOPHILES 18 1.3.1.4 HALOGEN NUCLEOPHILES 24 1.3.1.5 REDUCTIONS 25 1.3.2 CYCLOADDITION REACTIONS AND REARRANGEMENTS 25 1.3.2.1 AZIRIDINES IN [3 + 2] CYCLOADDITIONS 26 1.3.2.2 AZIRIDINES IN [2,3]-WITTIG REARRANGEMENTS 27 1.3.2.3 AZIRIDINES IN IODIDE-MEDIATED REARRANGEMENTS 27 1.3.2.4 AZIRIDINES IN MISCELLANEOUS REARRANGEMENTS 28 1.3.3 SYNTHESIS OF NATURAL PRODUCTS INVOLVING THE TRANSFORMATION OF AN AZIRIDINIUM MOIETY 31 BIBLIOGRAFISCHE INFORMATIONEN HTTP://D-NB.INFO/1009639870 DIGITALISIERT DURCH IMAGE 2 VI CONTENTS 1.4 CONCLUSION 32 REFERENCES 33 2 AZETIDINE AND ITS DERIVATIVES 41 HIDEMI YODA, MASAKI TAKAHASHI AND TETSUYA SENGOKU 2.1 INTRODUCTION 41 2.2 STRUCTURAL DESCRIPTION OF AZETIDINES 41 2.3 SYNTHETIC METHODOLOGIES FOR THE FORMATION OF AZETIDINE RINGS 43 2.4 SYNTHESIS OF MUGINEIC ACIDS 44 2.5 SYNTHESIS OF PENARESIDINS 46 2.6 STRUCTURAL DESCRIPTION OF AZETIDIN-2-ONES 50 2.7 SYNTHETIC METHODOLOGIES FOR THE FORMATION OF AZETIDIN-2-ONES 50 2.8 SYNTHESIS OF PENICILLIN 52 2.9 SYNTHESIS OF CEPHALOSPORIN 54 2.10 CONCLUSION 56 ACKNOWLEDGMENT 56 REFERENCES 57 3 EPOXIDES AND OXETANES 63 BISWANATH DAS AND KONGARA DAMODAR 3.1 INTRODUCTION 63 3.2 EPOXIDES IN NATURAL PRODUCT SYNTHESIS 63 3.2.1 SYNTHESIS OF NATURAL PRODUCTS POSSESSING AN EPOXIDE MOIETY 68 3.2.1.1 SYNTHESIS OF (-)-POSTIDURE 68 3.2.1.2 SYNTHESIS OF NATURAL POLYETHERS 68 3.2.1.3 SYNTHESIS OF (+)-LL,12-EPOXYSARCOPHYTOL A 68 3.2.1.4 SYNTHESIS OF (-)-SCYPHOSTATINE 68 3.2.1.5 SYNTHESIS OF ARENASTATIN A 70 3.2.1.6 SYNTHESIS OF (+)-AMBUIC ACID 70 3.2.1.7 TOTAL SYNTHESIS OF EPOCARBAZOLIN A 71 3.2.1.8 SYNTHESIS OF MULTIPLOLIDE A 71 3.2.2 SYNTHESIS OF NATURAL PRODUCTS INVOLVING THE TRANSFORMATION OF THE EPOXIDE MOIETY 71 3.2.2.1 SYNTHESIS OF DODONEINE 71 3.2.2.2 SYNTHESIS OF (-)-PERICOSIN B 73 3.2.2.3 SYNTHESIS OF (-)-PEUCEDANOL 73 3.2.2.4 SYNTHESIS OF (-H)-BOURGEANIC ACID 74 3.2.2.5 SYNTHESIS OF (6S)-5,6-DIHYDRO-6([2R]-2-HYDROXY-6-PHENYLHEXYL)-2H- PYRAN-2-ONE 74 3.2.2.6 SYNTHESIS OF VERBALACTONE 74 3.2.2.7 SYNTHESIS OF (2S, 3S)-(+)-AZIRIDINE-2,3-DICARBOXYLIC ACID 75 3.2.2.8 SYNTHESIS OF D-ERYTFTRO-SPHINGOSINE 75 3.2.2.9 SYNTHESIS OF (+)-L-733,060 76 3.2.2.10 SYNTHESIS OF (+)-CHELIDONINE 76 3.2.2.11 SYNTHESIS OF (-)-PIRONETIN 76 IMAGE 3 CONTENTS VII 3.2.2.12 SYNTHESIS OF (-)-CODONOPSININE 77 3.2.2.13 SYNTHESIS OF SESAMIN AND DIHYDROSESAMIN 77 3.2.2.14 SYNTHESIS OF (9S, 12R, 13S)-PINELLIC ACID 78 3.2.2.15 SYNTHESIS OF (Z)-NONENOLIDE 78 3.2.2.16 SYNTHESIS OF (-)-CUBEBOL 79 3.2.2.17 SYNTHESIS OF (+)-SCHWEINFURTHINS B AND E 79 3.2.2.18 SYNTHESIS OF (-)-CLEISTENOLIDE 80 3.2.2.19 SYNTHESIS OF DECARESTRICINE J 80 3.2.2.20 SYNTHESIS OF (-)-GLOEOSPORONE 82 3.2.2.21 SYNTHESIS OF (S)-DIHYDROKAVAIN 82 3.2.2.22 SYNTHESIS OF (-)-PHOROCANTHOLIDE-J 83 3.3 OXETANE IN NATURAL PRODUCT SYNTHESIS 85 3.3.1 SYNTHESIS OF NATURAL PRODUCTS POSSESSING AN OXETANE MOIETY 85 3.3.1.1 SYNTHESIS OF EPI-OXETIN 85 3.3.1.2 SYNTHESIS OF DIOXATRICYDIC SEGMENT OF DICTYOXETANE 86 3.3.1.3 SYNTHESIS OF (-)-MERRILACTONE A 86 3.3.1.4 TOTAL SYNTHESIS OF (+)-(Z)-LAUREATIN 87 3.3.1.5 SYNTHESIS OF TAXOL 87 3.3.2 SYNTHESIS OF NATURAL PRODUCTS INVOLVING TRANSFORMATION OF THE OXETANE MOIETY 88 3.3.2.1 SYNTHESIS OF EROGORGIAENE 88 3.3.2.2 SYNTHESIS OF TRANS- WHISKEY LACTONE 88 3.3.2.3 SYNTHESIS OF ()-SARRACENIN 89 3.4 CONCLUSION 89 ACKNOWLEDGMENT 90 REFERENCES 90 PART TWO COMMON RING HETEROCYCLES IN NATURAL PRODUCT SYNTHESIS 97 4 FURAN AND ITS DERIVATIVES 99 ALICIA BOTO AND LAURA ALVAREZ 4.1 INTRODUCTION 99 4.2 NATURAL PRODUCTS CONTAINING THE FURAN RING 100 4.2.1 OCCURRENCE OF FURAN RINGS IN NATURAL PRODUCTS 100 4.2.2 SYNTHESIS OF FURANS IN NATURAL PRODUCTS 104 4.3 FURAN DERIVATIVES AS REAGENTS IN THE SYNTHESIS OF NATURAL PRODUCTS 106 4.3.1 METALLATION 107 4.3.2 REDUCTION AND OXIDATION 111 4.3.3 FURAN DERIVATIVES AS ELECTROPHILES AND NUCLEOPHILES 138 4.3.4 FURAN IN CYCLOADDITIONS 124 4.3.4.1 [2 + 1], [2 + 2] AND [3 + 2] CYCLOADDITIONS 124 4.3.4.2 DIELS-ALDER ([4 + 2] CYDOADDITIONS) 127 IMAGE 4 VIII CONTENTS 4.3.4.3 [4 + 3], [6 + 4], [8 + 2] AND [5 + 2] CYCLOADDITIONS 133 4.3.5 FURAN IN OTHER REACTIONS 136 4.3.6 OTHER USES OF FURAN IN SYNTHESIS 138 4.4 SUMMARY 139 REFERENCES 140 5 PYRAN AND ITS DERIVATIVES 153 HIDETO MIYABE, OKIKO MIYATA AND TAKEAKI NAITO 5.1 INTRODUCTION 153 5.2 APPLICATION OF PYRAN MOIETIES IN THE SYNTHESIS OF NATURAL PRODUCTS 158 5.2.1 2,6-DISUBSTITUTED PYRAN NATURAL PRODUCTS 158 5.2.2 2,6-CYCLIC PYRAN COMPOUNDS 161 5.2.3 COMPLEX PYRAN NATURAL PRODUCTS 265 5.2.4 FUSED PYRAN COMPOUNDS WITH AROMATIC RINGS 168 5.2.5 FUSED PYRAN COMPOUNDS WITH ALIPHATIC RINGS 171 5.3 CONCLUSION 176 REFERENCES 176 6 PYRROLE AND ITS DERIVATIVES 287 DIPAKRANJAN MAI, BRATEEN SHOME AND BIDYUT KUMAR DINDA 6.1 INTRODUCTION 187 6.2 SYNTHESIS OF PYRROLE NATURAL PRODUCTS 193 6.2.1 MONOPYRROLIC NATURAL PRODUCTS 193 6.2.2 DIPYRROLIC NATURAL PRODUCTS 203 6.2.3 TRIPYRROLIC NATURAL PRODUCTS: PRODIGIOSINS 205 6.3 SYNTHESIS OF NON-PYRROLE NATURAL PRODUCTS FROM PYRROLE DERIVATIVES 209 6.4 CONCLUSION 214 ACKNOWLEDGMENTS 214 REFERENCES 225 7 INDOLES AND INDOLIZIDINES 221 SARAH M. BRONNER, C.-YOONJ. IM AND NEIL K. CARG 7.1 INTRODUCTION 221 7.2 APPLICATIONS OF INDOLES AND INDOLIZIDINES IN THE SYNTHESIS OF NATURAL PRODUCTS 222 7.2.1 INDOLES AND OXINDOLES 222 7.2.1.1 TOTAL SYNTHESIS OF ACTINOPHYLLIC ACID (OVERMAN) 222 7.2.1.2 TOTAL SYNTHESIS OF DRAGMACIDIN F (STOLTZ) 226 7.2.1.3 TOTAL SYNTHESIS OF PENITREM D (SMITH) 230 7.2.1.4 TOTAL SYNTHESIS OF WELWITINDOLINONE A ISONITRILE (BARAN, WOOD) 232 7.2.2 INDOLINES 237 7.2.2.1 TOTAL SYNTHESIS OF LL.LL'-DIDEOXYVERTICILLIN A (MOVASSAGHI) 237 IMAGE 5 CONTENTS IX 7.2.2.2 TOTAL SYNTHESIS OF MINFIENSINE (OVERMAN, QIN, MACMILLAN) 240 7.2.2.3 TOTAL SYNTHESIS OF NORFLUOROCURARINE (VANDERWAL) 245 7.2.2.4 TOTAL SYNTHESIS OF PSYCHOTRIMINE (BARAN) 247 7.2.3 INDOLIZIDINES 249 7.2.3.1 TOTAL SYNTHESIS OF MYRMICARINS 215A, 215B AND 217 (MOVASSAGHI) 249 7.2.3.2 TOTAL SYNTHESIS OF SERRATEZOMINE A (JOHNSTON) 252 7.3 CONCLUSION 254 ACKNOWLEDGMENT 254 REFERENCES 254 8 PYRIDINE AND ITS DERIVATIVES 267 PAULA KIURU ANDJARI YLI-KAUHALUOMA 8.1 INTRODUCTION 267 8.2 APPLICATION OF THE PYRIDINE MOIETY IN THE SYNTHESIS OF NATURAL PRODUCTS 268 8.2.1 PYRIDINES 268 8.2.1.1 SYNTHESIS OF NORANABASAMINE ENANTIOMERS 268 8.2.1.2 SYNTHESIS OF QUATERPYRIDINE NEMERTELLINE 268 8.2.1.3 SYNTHESIS OF CAERULOMYCIN C 276 8.2.1.4 SYNTHESIS OF THE SPONGIDINE ISOMER 277 8.2.2 2-ALKYLPYRIDINES 278 8.2.2.1 SYNTHESIS OF MONTIPYRIDINE 278 8.2.2.2 SYNTHESIS OF PIERIDDIN AL 278 8.2.3 3-ALKYLPYRIDINE, 3-ALKYLPYRIDINIUM AND 3-ALKYLTETRAHYDROPYRIDINE COMPOUNDS 281 8.2.3.1 SYNTHESIS OF XESTAMINES 281 8.2.3.2 SYNTHESIS OF PYRINADINE A 282 8.2.3.3 SYNTHESIS OF PYRINODEMIN A 282 8.2.3.4 SYNTHESIS OF HALIDAMINE A 284 8.2.4 PIPERIDINES 285 8.2.4.1 SYNTHESIS OF CONIINE AND PIPECOLINE 285 8.2.4.2 SYNTHESIS OF STENUSINE 286 8.2.5 PYRIDONES 287 8.2.5.1 SYNTHESIS OF ()-CYTISINE 287 8.2.5.2 SYNTHESIS OF IROMYCIN A 288 8.3 CONCLUSION 289 ACKNOWLEDGMENT 289 REFERENCES 290 9 QUINOLINES AND ISOQUINOLINES 299 ANTONIO CARRIDO MONTALBAN 9.1 INTRODUCTION 299 9.2 APPLICATION OF QUINOLINES AND ISOQUINOLINES IN THE SYNTHESIS OF NATURAL PRODUCTS 300 IMAGE 6 X CONTENTS 9.2.1 QUINOLINE-CONTAINING NATURAL PRODUCTS 308 9.2.1.1 QUININE 308 9.2.1.2 SANDRAMYCIN 311 9.2.1.3 LAVENDAMYCIN 313 9.2.2 ISOQUINOLINE-CONTAINING NATURAL PRODUCTS 317 9.2.2.1 MORPHINE 317 9.2.2.2 EMETINE 320 9.2.2.3 PROTOBERBERINES 326 9.2.2.4 NITIDINE 331 9.3 CONDUSION 332 REFERENCES 332 10 CARBAZOLES AND ACRIDINES 341 KONSTANZE K. GRUENER AND HANS-JOACHIM KNB'IKER 10.1 INTRODUCTION TO CARBAZOLES 341 10.2 TOTAL SYNTHESIS OF CARBAZOLE ALKALOIDS 341 10.2.1 PALLADIUM-CATALYZED SYNTHESIS OF CARBAZOLES 350 10.2.1.1 TOTAL SYNTHESIS OF PITYRIAZOLE 350 10.2.1.2 TOTAL SYNTHESIS OF EUCHRESTIFOLINE AND GIRINIMBINE 351 10.2.2 IRON-MEDIATED SYNTHESIS OF CARBAZOLES 353 10.2.2.1 TOTAL SYNTHESES OF THE ANTIOSTATINS 353 10.2.2.2 TOTAL SYNTHESIS OF R-(-)-NEOCARAZOSTATIN B AND CARQUINOSTATIN A 355 10.2.3 TOTAL SYNTHESES OF ELLIPTICINE AND STAUROSPORINONE 356 10.2.3.1 SYNTHESIS OF ELLIPTICINE 356 10.2.3.2 SYNTHESIS OF STAUROSPORINONE 357 10.3 INTRODUCTION TO ACRIDINES 358 10.4 SYNTHESIS OF ACRIDINES AND ACRIDONES 361 10.4.1 TOTAL SYNTHESIS OF ACRONYCINE 361 10.4.2 SYNTHESIS OF AMSACRINE 362 10.4.3 TOTAL SYNTHESES OF AMPHIMEDINE 362 REFERENCES 364 11 THIOPHENE AND OTHER SULFUR HETEROCYCLES 377 KRISHNA C. MAJUMDAR AND SHOVAN MONDAI 11.1 INTRODUCTION 377 11.2 SYNTHESIS OF NATURAL PRODUCTS CONTAINING THIOPHENE 378 11.2.1 SYNTHESIS OF NATURAL PRODUCTS FROM THIOPHENE-BASED SUBSTRATES 378 11.2.2 SYNTHESIS OF NATURAL PRODUCTS BY CONSTRUCTION OF THE THIOPHENE NUCLEUS 386 11.3 SYNTHESIS OF NATURAL PRODUCTS CONTAINING OTHER SULFUR HETEROCYCLES 393 11.4 CONCLUSION 395 ACKNOWLEDGMENTS 396 REFERENCES 397 IMAGE 7 CONTENTS XI 12 OXAZOLE AND ITS DERIVATIVES 403 DAVID W. KNIGHT 12.1 INTRODUCTION 403 12.2 MONO-OXAZOLES 404 12.2.1 PIMPRININ 404 12.2.2 TEXAMINE AND RELATIVES 405 12.2.3 SYNTHESIS OF SULFOMYCIN FRAGMENTS 406 12.2.4 AJUDAZOL A AND B 408 12.2.5 RHIZOXIN 409 12.2.6 THE CALYCULINS 410 12.2.7 LEUCASCANDROLIDE A, B AND NEOPELTOLIDE 413 12.2.8 CHIVOSAZOLE 416 12.2.9 MADUMYCIN II 416 12.2.10 14,15-ANHYDROPRISTINAMYCIN II B 428 12.2.11 GRISEOVIRIDIN 428 12.2.12 THIANGAZOLE 419 12.3 UNCONNECTED BIS- AND TRIS-OXAZOLES 420 12.3.1 DISORAZOLEQ 420 12.3.2 PHORBOXAZOLES 422 12.3.3 LEUCAMIDE A 424 12.3.4 PROMOTHIOCIN A 425 12.3.5 BERNINAMYCIN A 425 12.4 CYDIC POLYHETEROCYDIC METABOLITES CONTAINING SINGLE OXAZOLE RESIDUES 426 12.4.1 DENDROAMIDE A 426 12.4.2 NOSTOCYDAMIDE 427 12.4.3 BISTRATAMIDES 428 12.4.4 TENUECYCLAMIDES A-D 428 12.4.5 DOLASTATIN I 429 12.5 CONJUGATED BIS-OXAZOLES 429 12.5.1 (-)-HENNOXAZOLE A 429 12.5.2 MUSCORIDE A 432 12.5.3 DIAZONAMIDE A 433 12.5.4 BENGAZOLE A 437 12.5.5 SIPHONAZOLE 439 12.6 TRIS- AND POLY-OXAZOLES 440 12.6.1 ULAPUALIDE A 440 12.6.2 (R)-TELOMESTATIN 443 12.6.3 IB-01211 445 12.6.4 YM-216391 445 REFERENCES 446 13 THIAZOLINE AND THIAZOLE AND THEIR DERIVATIVES 459 ZHENGSHUANG XU AND TAO YE 13.1 INTRODUCTION 459 IMAGE 8 XII I CONTENTS 13.2 GENERAL METHODS FOR THE SYNTHESIS OF THIAZOLINE AND THIAZOLE DERIVATIVES 460 13.2.1 METHODS FOR THE PREPARATION OF THIAZOLINES 460 13.2.1.1 USING VICINAL AMINO THIOLS AS STARTING MATERIALS 461 13.2.1.2 FROM VICINAL AMINO ALCOHOL 468 13.2.1.3 MISCELLANEOUS 473 13.2.2 METHODS FOR PREPARATION OF THIAZOLES 474 13.2.2.1 DEHYDROGENATION OF THIAZOLINES OR THIAZOLIDINES 474 13.2.2.2 THE HANTZSCH METHOD AND ITS MODIFICATIONS 479 13.2.2.3 ALKYLATION OF THIAZOLE OR THIAZOLE DERIVATIVES 483 13.2.2.4 MISCELLANEOUS 483 13.3 THIAZOLE AND THIAZOLINE-CONTAINING NATURAL PRODUCTS 485 13.3.1 THIAZOLINE AND THIAZOLE EMBEDDED IN POLYKETIDES 485 13.3.2 THIAZOLINE AND THIAZOLE EMBEDDED IN PEPTIDES 491 13.4 CONCLUSIONS 494 REFERENCES 494 14 PYRIMIDINE AND IMIDAZOLE 507 VIPAN KUMAR AND MOHINDER P. MAHAJAN 14.1 GENERAL INTRODUCTION 507 14.2 PYRIMIDINE-BASED NATURAL PRODUCTS 507 14.2.1 INTRODUCTION 507 14.2.2 SYNTHESIS OF PYRIMIDINE-BASED NATURAL PRODUCTS 508 14.3 IMIDAZOLE-BASED NATURAL PRODUCTS 518 14.3.1 INTRODUCTION 518 14.3.2 SYNTHESIS OF IMIDAZOLE-BASED NATURAL PRODUCTS 520 14.4 CONCLUSION 527 ACKNOWLEDGMENT 528 REFERENCES 529 PART THREE NATURAL PRODUCTS CONTAINING MEDIUM AND LARGE RING- SIZED HETEROCYDIC SYSTEMS 535 15 OXEPINES AND AZEPINES 537 DARREN L. RILEY AND WILLEM A.L. VAN OTTERLO 15.1 INTRODUCTION 537 15.2 SYNTHESIS OF THE HETEROCYDIC CORE OF SELECTED NATURAL PRODUCTS CONTAINING OXEPINES 538 15.3 SYNTHESIS OF THE HETEROCYDIC CORE OF SELECTED NATURAL PRODUCTS CONTAINING AZEPINES 549 15.4 SYNTHESIS OF THE HETEROCYDIC CORE OF SELECTED NATURAL PRODUCTS CONTAINING OXAZAPINES 559 15.5 CONCLUSION 561 IMAGE 9 CONTENTS I XIII ACKNOWLEDGMENTS 562 REFERENCES 562 16 BIOACTIVE MACROCYCLIC NATURAL PRODUCTS 569 SITI MARIAM MOHD NOR, ZHENGSHUANG XU AND TOO YE 16.1 GENERAL 569 16.2 NATURAL PRODUCTS CONTAINING AZOLES 569 16.2.1 APRATOXIN A 569 16.2.2 HALIPEPTINS A AND D 572 16.2.3 LARGAZOLE 573 16.2.4 BISTRATAMIDE H AND DIDMOLAMIDE A 575 16.2.5 IB-01211 576 16.2.6 (R)-TELOMESTATIN 578 16.3 PYRIDINE- AND PIPERIDINE-CONTAINING NATURAL PRODUCTS 581 16.3.1 MICROCOCCIN PI 581 16.3.2 GE2270S 584 16.4 INDOLE- AND IMIDAZOLE-CONTAINING NATURAL PRODUCTS 587 16.4.1 CELOGENTIN C 587 16.4.2 COMPLESTATIN (CHLOROPEPTIN II) 589 16.5 PYRAN- AND FURAN-CONTAINING NATURAL PRODUCTS 590 16.5.1 PHORBOXAZOLE B 590 16.5.2 SORANGICIN A 592 16.5.3 KENDOMYCIN 594 16.5.4 BRYOSTATIN 16 597 16.5.5 IKD-8344 598 16.5.6 DEOXYPUKALIDE 599 16.5.7 NORHALICHONDRIN B 601 16.6 PIPERAZIC ACID-CONTAINING NATURAL PRODUCTS 605 16.6.1 PIPERAZIMYCIN A 605 16.6.2 AZINOTHRICIN AND KETTAPEPTIN 607 16.7 MIXED HETEROCYDIC SYSTEMS 608 16.7.1 (-)-NAKADOMARIN A 608 16.8 CONCLUSIONS 610 REFERENCES 611 INDEX 622
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id DE-604.BV039132485
illustrated Illustrated
indexdate 2024-11-25T17:37:10Z
institution BVB
isbn 9783527327065
language English
oai_aleph_id oai:aleph.bib-bvb.de:BVB01-024150774
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physical XX, 637 S. graph. Darst.
publishDate 2011
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publisher Wiley-VCH-Verl.
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spellingShingle Heterocycles in natural product synthesis
Heterocyclische Verbindungen (DE-588)4159726-6 gnd
Chemische Synthese (DE-588)4133806-6 gnd
Naturstoff (DE-588)4041418-8 gnd
subject_GND (DE-588)4159726-6
(DE-588)4133806-6
(DE-588)4041418-8
title Heterocycles in natural product synthesis
title_auth Heterocycles in natural product synthesis
title_exact_search Heterocycles in natural product synthesis
title_full Heterocycles in natural product synthesis ed. by Krishna C. Majumdar and Shital K. Chattopadhyay
title_fullStr Heterocycles in natural product synthesis ed. by Krishna C. Majumdar and Shital K. Chattopadhyay
title_full_unstemmed Heterocycles in natural product synthesis ed. by Krishna C. Majumdar and Shital K. Chattopadhyay
title_short Heterocycles in natural product synthesis
title_sort heterocycles in natural product synthesis
topic Heterocyclische Verbindungen (DE-588)4159726-6 gnd
Chemische Synthese (DE-588)4133806-6 gnd
Naturstoff (DE-588)4041418-8 gnd
topic_facet Heterocyclische Verbindungen
Chemische Synthese
Naturstoff
url http://deposit.dnb.de/cgi-bin/dokserv?id=3655691&prov=M&dok_var=1&dok_ext=htm
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