A FACILE CHIRAL APPROACH TO THE DENDROBINE SKELETON BY INTRAMOLECULAR PAUSON-KHAND REACTION

被引:45
作者
TAKANO, S
INOMATA, K
OGASAWARA, K
机构
关键词
D O I
10.1246/cl.1992.443
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A possible chiral synthetic route to the alkaloid (-)-dendrobine has been explored by employing intramolecular Pauson-Khand reaction as the key step. The cobalt complex generated from (S)-carvone yielded a single stereoisomer (10) on intramolecular Pauson-Khand reaction. The adduct 10 was transformed into decarboxy-7,9-dihydrodendrobine by a four-step reaction.
引用
收藏
页码:443 / 446
页数:4
相关论文
共 25 条
  • [1] SYNTHETIC APPROACH TO DENDROBINE SKELETON
    BRATTESANI, DN
    HEATHCOCK, CH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (15) : 2165 - 2170
  • [2] THE SYNTHESIS OF NITROGEN-HETEROCYCLES VIA THE INTRAMOLECULAR KHAND REACTION - FORMATION OF TETRA-HYDROCYCLOPENTA[C]PYRROL-5(1H)-ONES AND HEXA-HYDROCYCLOPENTA[C]PYRROL-5(1H)-ONES AND HEXAHYDRO-6H-2-PYRINDIN-6-ONES
    BROWN, SW
    PAUSON, PL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04): : 1205 - 1209
  • [3] A FACILE AND SELECTIVE 1,2-REDUCTION OF CONJUGATED KETONES WITH NABH4 IN THE PRESENCE OF CACL2
    FUJII, H
    OSHIMA, K
    UTIMOTO, K
    [J]. CHEMISTRY LETTERS, 1991, (10) : 1847 - 1848
  • [4] TOTAL SYNTHESIS OF ALKALOID (+/- )-DENDROBINE
    INUBUSHI, Y
    IBUKA, T
    TANAKA, K
    TOKANE, K
    SAJI, I
    KIKUCHI, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (22) : 1252 - &
  • [5] INUBUSHI Y, 1974, CHEM PHARM BULL, V22, P349
  • [6] INUBUSHI Y, 1963, J PHARM SOC JAPAN, V83, P1184
  • [7] AN EFFICIENT PREPARATION OF 3-AZABICYCLO[3.3.0]OCT-5-EN-7-ONES FROM PROPARGYL ALCOHOL-COBALT COMPLEXES VIA NICHOLAS REACTION WITH AMIDIC NITROGEN NUCLEOPHILES FOLLOWED BY PAUSON-KHAND CYCLIZATION
    JEONG, N
    YOO, SE
    LEE, SJ
    LEE, SH
    CHUNG, YK
    [J]. TETRAHEDRON LETTERS, 1991, 32 (19) : 2137 - 2140
  • [8] SIMPLE TOTAL SYNTHESIS OF (+/-)-DENDROBINE
    KENDE, AS
    BENTLEY, TJ
    MADER, RA
    RIDGE, D
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (13) : 4332 - 4334
  • [9] ORGANOCOBALT COMPLEXES .2. REACTION OF ACETYLENEHEXACARBONYLDICOBALT COMPLEXES, (R1C2R2)CO2(CO)6, WITH NORBORNENE AND ITS DERIVATIVES
    KHAND, IU
    KNOX, GR
    PAUSON, PL
    WATTS, WE
    FOREMAN, MI
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (09): : 977 - 981
  • [10] THE DIRECTED PAUSON-KHAND REACTION
    KRAFFT, ME
    JULIANO, CA
    SCOTT, IL
    WRIGHT, C
    MCEACHIN, MD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) : 1693 - 1703