Asymmetric synthesis of alkannin and shikonin.

被引：31
作者：
Couladouros, EA
Plyta, ZF
Strongilos, AT
Papageorgiou, VP
机构：
[1] NCSR DEMOKRITOS, ORGAN & BIOORGAN CHEM LAB, ATHENS, GREECE
[2] ARISTOTELIAN UNIV THESSALONIKI, DEPT CHEM ENGN, ORGAN CHEM LAB, THESSALONIKI 54006, GREECE
来源：
TETRAHEDRON LETTERS | 1997年 / 38卷 / 41期
关键词：
D O I：
10.1016/S0040-4039(97)01687-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new general and convergent route for the synthesis of the title compounds is presented. The polyoxygenated aromatic ring system is annulated in one operation by the condensation of a Michael type acceptor with an 1,4 dipole equivalent. The chiral center of the target is introduced via an asymmetric allyl boration in high ee. Overall, the fully protected natural product is constructed within 8 steps in 35% total yield. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码：7263 / 7266
页数：4
相关论文
共 41 条
  • [1] SHIKONIN BETA,BETA-DIMETHYLACRYLATE - A COMPONENT OF ALKANNA-HIRSUTISSIMA
    AFZAL, M
    MUHAMMAD, N
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1983, 47 (02): : 411 - 412
  • [2] ACYLSHIKONIN ANALOGS - SYNTHESIS AND INHIBITION OF DNA TOPOISOMERASE-I
    AHN, BZ
    BAIK, KU
    KWEON, GR
    LIM, K
    HWANG, BD
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (06) : 1044 - 1047
  • [3] BRAUN M, 1991, LIEBIGS ANN CHEM, P1157
  • [4] Brockmann H, 1936, LIEBIGS ANN CHEM, V521, P1
  • [5] DIISOPINOCAMPHEYLCHLOROBORANE, A REMARKABLY EFFICIENT CHIRAL REDUCING AGENT FOR AROMATIC PROCHIRAL KETONES
    CHANDRASEKHARAN, J
    RAMACHANDRAN, PV
    BROWN, HC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) : 5446 - 5448
  • [6] ANNELATION REACTIONS OF QUINONE MONOKETALS - STUDIES DIRECTED AT AN EFFICIENT SYNTHESIS OF ANTHRACYCLINONES
    CHENARD, BL
    DOLSON, MG
    SERCEL, AD
    SWENTON, JS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (02) : 318 - 325
  • [7] DIOSCURIDIS P, 1958, MAT MED, V4, P187
  • [8] INDUCTION OF TOPOISOMERASE-II-MEDIATED DNA CLEAVAGE BY THE PLANT NAPHTHOQUINONES PLUMBAGIN AND SHIKONIN
    FUJII, N
    YAMASHITA, Y
    ARIMA, Y
    NAGASHIMA, M
    NAKANO, H
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1992, 36 (12) : 2589 - 2594
  • [9] FORMATION OF STEREOISOMERIC MIXTURES OF NAPHTHOQUINONE DERIVATIVES IN ECHIUM-LYCOPSIS CALLUS-CULTURES
    FUKUI, H
    TSUKADA, M
    MIZUKAMI, H
    TABATA, M
    [J]. PHYTOCHEMISTRY, 1983, 22 (02) : 453 - 456
  • [10] GUNTHER R, 1959, GREEK HERBAL DIOSCOR, V4, P421
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