Total synthesis and stereochemistry of 13-hydroxy-α-eudesmol

被引:14
|
作者
Chen, YG
Xiong, ZM
Zhou, G
Liu, LJ
Li, YL [1 ]
机构
[1] Lanzhou Univ, Natl Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Lanzhou Univ, Inst Organ Chem, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0957-4166(98)00184-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The first total synthesis of both C-11 epimers of 13-hydroxy-alpha-eudesmol 1a and 1b by the use, as a key reaction, of the Sharpless asymmetric dihydroxylation of alkene 7 is presented. The absolute configuration of natural 13-hydroxy-alpha-eudesmol is established through comparison of the H-1 NMR spectrum of natural diol and synthetic diols. In our synthesis another natural product (+)-alpha-selinene 2 has also been accomplished. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1923 / 1928
页数:6
相关论文
共 50 条
  • [21] Total synthesis and stereochemistry of (-)-cacospongionolide F
    Demeke, D
    Forsyth, CJ
    ORGANIC LETTERS, 2003, 5 (07) : 991 - 994
  • [22] Total Synthesis and Absolute Stereochemistry of Seragakinone A
    Takada, Akiomi
    Hashimoto, Yoshimitsu
    Takikawa, Hiroshi
    Hikita, Katsuyoshi
    Suzuki, Keisuke
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (10) : 2297 - 2301
  • [23] Total synthesis and stereochemistry of mycolactone F
    Kim, Han-Je
    Kishi, Yoshito
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (06) : 1842 - +
  • [24] Total synthesis and stereochemistry establishment of tumescenamide A
    Xue, Hong
    Fan, Shiming
    Xu, Jingzhe
    Liu, Shouxin
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (06) : 1675 - 1679
  • [25] STUDIES ON THE BIOSYNTHESIS OF ALIPHATIC LACTONES IN SPOROBOLOMYCES-ODORUS - CONVERSION OF (S)-13-HYDROXY-(Z,E)-9,11-OCTADECADIENOIC ACID AND (R,S)-13-HYDROXY-(Z,E)-9,11-OCTADECADIENOIC ACID INTO OPTICALLY PURE (R)-DELTA-DECALACTONE
    ALBRECHT, W
    SCHWARZ, M
    HEIDLAS, J
    TRESSL, R
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07): : 1954 - 1956
  • [26] SYNTHESIS OF (+)-ALPHA-EUDESMOL
    HUMBER, DC
    PINDER, AR
    TETRAHEDRON LETTERS, 1966, (41) : 4985 - &
  • [27] MACROCYCLIC PYRROLIZIDINE ALKALOIDS - SYNTHESIS AND STEREOCHEMISTRY OF (+)-DICROTALINE (13-BETA-HYDROXY-13-ALPHA-METHYL-1,2-DIDEHYDROCROTALANINE) AND (+)-13-EPI-DICROTALINE
    BROWN, K
    DEVLIN, JA
    ROBINS, DJ
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08): : 1819 - 1824
  • [28] Total synthesis and absolute stereochemistry of plakortone E
    Akiyama, M
    Isoda, Y
    Nishimoto, M
    Narazaki, M
    Oka, H
    Kuboki, A
    Ohira, S
    TETRAHEDRON LETTERS, 2006, 47 (14) : 2287 - 2290
  • [29] TOTAL SYNTHESIS OF (+/-)-VIRANTMYCIN AND DETERMINATION OF ITS STEREOCHEMISTRY
    MORIMOTO, Y
    MATSUDA, F
    SHIRAHAMA, H
    SYNLETT, 1991, (03) : 201 - 203
  • [30] Total synthesis and stereochemistry revision of mannopeptimycin aglycone
    Fuse, Shinichiro, 1600, American Chemical Society (136):