ASYMMETRIC-SYNTHESIS OF (-)-NEOPODOPHYLLOTOXIN

被引:53
作者
CHARLTON, JL
KOH, K
机构
[1] Department of Chemistry, University of Manitoba, Winnipeg, Manitoba
关键词
D O I
10.1021/jo00031a033
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A five-step asymmetric synthesis of neopodophyllotoxin in 18% overall yield and optical purity > 97%, starting from 6-(3,4,5-trimethoxybenzyl)piperonal (6) and the fumarate of (S)-methyl mandelate (8), is described.
引用
收藏
页码:1514 / 1516
页数:3
相关论文
共 27 条
  • [1] ASYMMETRIC TOTAL SYNTHESIS OF (-)-PODOPHYLLOTOXIN
    ANDREWS, RC
    TEAGUE, SJ
    MEYERS, AI
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) : 7854 - 7858
  • [2] PHOTOCHEMICAL REACTIONS .1. NEW ROUTE TO TETRADEHYDROPODO-PHYLLOTOXIN, TAIWANIN E, AND RELATED COMPOUNDS
    ARNOLD, BJ
    MELLOWS, SM
    SAMMES, PG
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (12): : 1266 - 1270
  • [3] CHARLTON JL, 1990, SYNLETT, P333
  • [4] ASYMMETRIC-SYNTHESIS OF PODOPHYLLOTOXIN ANALOGS
    CHARLTON, JL
    PLOURDE, GL
    KOH, K
    SECCO, AS
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (11): : 2022 - 2027
  • [5] DIELS-ALDER ADDITION OF THE FUMARATE AND ACRYLATE OF S-METHYL LACTATE TO ALPHA-HYDROXY ORTHOQUINODIMETHANES
    CHARLTON, JL
    PLOURDE, GL
    KOH, K
    SECCO, AS
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1989, 67 (04): : 574 - 579
  • [6] AN ENANTIOSELECTIVE TOTAL SYNTHESIS OF EPIISOPODOPHYLLOTOXIN
    CHOY, W
    [J]. TETRAHEDRON, 1990, 46 (07) : 2281 - 2286
  • [7] DOYLE TW, 1984, ETOPOSIDE VP16 CURRE
  • [8] COMPREHENSIVE SYNTHETIC ROUTE TO 8 DIASTEREOMERIC PODOPHYLLUM LIGNANS
    FORSEY, SP
    RAJAPAKSA, D
    TAYLOR, NJ
    RODRIGO, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (18) : 4280 - 4290
  • [9] SYNTHESIS OF PODOPHYLLOTOXIN
    GENSLER, WJ
    GATSONIS, CD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) : 4004 - &
  • [10] SYNTHESIS OF (+/-)-EPIISOPODOPHYLLOTOXIN
    GLINSKI, MB
    DURST, T
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (03): : 573 - 575