A COMMON INTERMEDIATE PROVIDING SYNTHESES OF PSI-TABERSONINE, CORONARIDINE, IBOXYPHYLLINE, IBOPHYLLIDINE, VINAMIDINE, AND VINBLASTINE

被引：83

作者：

BORNMANN, WG ^{[1
]}

KUEHNE, ME ^{[1
]}

机构：

[1] UNIV VERMONT,DEPT CHEM,BURLINGTON,VT 05405

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 06期

关键词：

D O I：

10.1021/jo00032a029

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Generation of the key tetracyclic intermediates 14a,b in six steps (42% overall) and subsequent short reduction, oxidation, and arylation sequences results in total syntheses of the title compounds 8, 9, 10, 11, 12, and 13.

引用

页码：1752 / 1760

页数：9

共 29 条

[1]

STRUCTURE OF CATHARININE - BIS-INDOLE ALKALOID ISOLATED FROM SEVERAL SPECIES OF CATHARANTHUS [J].

ANDRIAMIALISOA, RZ ;

LANGLOIS, N ;

POTIER, P ;

CHIARONI, A ;

RICHE, C .

TETRAHEDRON, 1978, 34 (06) :677-683

[2]

ATTAURRAHMAN, 1978, Patent No. 126852

[3]

REARRANGEMENT OF CATHARANTHINE, STEMMADENINE AND TABERSONINE IN ACETIC ACID [J].

BROWN, RT ;

HILL, JS ;

SMITH, GF ;

STAPLEFO.KS .

TETRAHEDRON, 1971, 27 (21) :5217-&

[4]

BEYOND ERYTHRO AND THREO - A PROPOSAL FOR SPECIFYING RELATIVE CONFIGURATION IN MOLECULES WITH MULTIPLE CHIRAL CENTERS [J].

CAREY, FA ;

KUEHNE, ME .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (20) :3811-3815

[5]

HOIZEY MJ, 1974, TETRAHEDRON LETT, V17, P1601

[6]

Kuehne M. E., 1990, ALKALOIDS, V37, P77

[7]

BIOMIMETIC SYNTHESES OF INDOLE ALKALOIDS .11. SYNTHESES OF BETA-CARBOLINE AND INDOLOAZEPINE INTERMEDIATES [J].

KUEHNE, ME ;

BOHNERT, JC ;

BORNMANN, WG ;

KIRKEMO, CL ;

KUEHNE, SE ;

SEATON, PJ ;

ZEBOVITZ, TC .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (07) :919-924

[8]

STUDIES IN BIOMIMETIC ALKALOID SYNTHESES .5. TOTAL SYNTHESES OF PSI-VINCADIFFORMINE, 20-EPI-PSI-VINCADIFFORMINE, PANDOLINE, 20-EPIPANDOLINE, AND THE C-16 EPIMERIC (CARBOMETHOXY)VELBANAMINES [J].

KUEHNE, ME ;

KIRKEMO, CL ;

MATSKO, TH ;

BOHNERT, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (16) :3259-3265

[9]

SYNTHESES OF 20'-DEOXYVINBLASTINE, 20'-DEOXYLEUROSIDINE, 20'-DEOXYVINCOVALINE, 20'-EPI-20'-DEOXYVINCOVALINE, AND 20'-DEOXYVINCRISTINE AND ITS 20'-EPIMER THROUGH RACEMIC AND ENANTIOSELECTIVELY GENERATED INTERMEDIATES - NEW SYNTHESES OF D/E-CIS-PSEUDO-VINCADIFFOMINES AND D/E-TRANS-PSEUDO-VINCADIFFORMINES AND D/E-CIS-20-EPI-PSEUDO-VINCADIFFORMINES AND D/E-TRANS-20-EPI-PSEUDO-VINCADIFFORMINESE [J].

KUEHNE, ME ;

BORNMANN, WG .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (14) :3407-3420

[10]

3 ROUTES TO THE CRITICAL C16'-C14' PARF RELATIVE STEREOCHEMISTRY OF VINBLASTINE - SYNTHESES OF 20'-DESETHYL-20'-DEOXYVINBLASTINE AND 20'-DESETHYL-20'-DEOXYVINCOVALINE [J].

KUEHNE, ME ;

ZEBOVITZ, TC ;

BORNMANN, WG ;

MARKO, I .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4340-4349

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