TOTAL SYNTHESIS OF (-)-CEPHALOTAXINE

被引：112

作者：

ISONO, N

MORI, M

机构：

[1] Faculty of Pharmaceutical Sciences, Hokkaido University

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 01期

关键词：

D O I：

10.1021/jo00106a023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of (-)-cephalotaxine was achieved from D-(+)-proline by a short sequence of steps. The key intermediate, 1-azaspiro[4.4]nonane, was prepared from vinyl iodide, using stannyl anion generated from Me(3)SiSnBu(3) and CsF, in good yield.

引用

页码：115 / 119

页数：5

共 32 条

[1] AOYAMA T, 1984, CHEM PHARM BULL, V32, P3759
[2] ALKALOIDS ISOLATED FROM CEPHALOTAXUS-DURPACEA SIEB ET ZUCC
ASADA, S
[J]. YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1973, 93 (07): : 916 - 924
[3] TOTAL SYNTHESIS OF CEPHALOTAXINE
AUERBACH, J
WEINREB, SM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (20) : 7172 - &
[4] AUERBACH J, 1975, J AM CHEM SOC, V97, P2503
[5] BECK AK, 1993, ORG SYNTH, V72, P62
[6] TOTAL SYNTHESIS OF DL-CEPHALOTAXINE - THE 1ST EXAMPLE OF AN INTRAMOLECULAR 4 + 2 CYCLO-ADDITION WHERE THE DIENOPHILE HAS BEEN DELIVERED FROM THE FACE OPPOSITE TO THE TETHERING MOIETY
BURKHOLDER, TP
FUCHS, PL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) : 2341 - 2342
[7] TOTAL SYNTHESIS OF THE CEPHALOTAXUS ALKALOIDS DL-CEPHALOTAXINE, DL-11-HYDROXYCEPHALOTAXINE, AND DL-DRUPACINE
BURKHOLDER, TP
FUCHS, PL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) : 9601 - 9613
[8] SILICON IN ORGANIC-SYNTHESIS - STEREOSELECTIVE SYNTHESIS OF SOME INSECT SEX-PHEROMONES
CHAN, TH
KOUMAGLO, K
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 285 (1-3) : 109 - 119
[9] SILYLSTANNANES IN ORGANIC-SYNTHESIS - SCOPE AND LIMITATION OF PALLADIUM-CATALYZED REACTION WITH ACETYLENES
CHENARD, BL
VANZYL, CM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) : 3561 - 3566
[10] NEW ROUTES TO FUNCTIONALIZED BENZAZEPINE SUBSTRUCTURES - A NOVEL TRANSFORMATION OF AN ALPHA-DIKETONE THIOAMIDE INDUCED BY TRIMETHYL PHOSPHITE
FANG, FG
MAIER, ME
DANISHEFSKY, SJ
SCHULTE, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03) : 831 - 838

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