Dichlorocarbene adducts of alkyl enol ethers as precursors to furans:: application to a total synthesis of the furanosesquiterpene (±)-pallescensin A

被引:28
作者
Foot, Jonathan S. [1 ]
Phillis, Andrew T. [1 ]
Sharp, Phillip P. [1 ]
Willis, Anthony C. [1 ]
Banwell, Martin G. [1 ]
机构
[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia
基金
澳大利亚研究理事会;
关键词
cyclopropene; dichlorocyclopropane; furan; furanosesquiterpene; pallescensin A; Wieland-Miescher ketone;
D O I
10.1016/j.tetlet.2006.07.068
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel method for annulating furans to ketones, involving treatment of the dichlorocarbene adduct of the derived methyl enol ether with base, has been exploited in the synthesis of the title natural product 1 from the known trans-decalone 2. Crown Copyright (c) 2006 Published by Elsevier Ltd. All rights reserved.
引用
收藏
页码:6817 / 6820
页数:4
相关论文
共 34 条
  • [1] AKITA H, 1981, CHEM PHARM BULL, V29, P1580
  • [2] FURANOSESQUITERPENE SYNTHESIS - AN UPDATED REVIEW
    ALLEN, AJ
    VAILLANCOURT, V
    ALBIZATI, KF
    [J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1994, 26 (01) : 1 - &
  • [3] SYNTHETIC APPROACHES TO PENTACYCLIC TRITERPENES OF THE ARBORANE FAMILY
    ARSENIYADIS, S
    RODRIGUEZ, R
    CABRERA, E
    THOMPSON, A
    OURISSON, G
    [J]. TETRAHEDRON, 1991, 47 (34) : 7045 - 7058
  • [4] Banwell M.G., 1991, ADV STRAIN ORGANIC C, V1, P19
  • [5] DEHYDROHALOGENATION OF THE BIS-DIHALOCARBENE ADDUCTS OF SOME METHOXYCYCLOHEXA-1,4-DIENES - REVISION OF PRODUCT STRUCTURES
    BANWELL, MG
    GABLE, RW
    HALTON, B
    PHYLAND, JR
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (10) : 1879 - 1884
  • [6] A proline-catalyzed asymmetric Robinson annulation reaction
    Bui, T
    Barbas, CF
    [J]. TETRAHEDRON LETTERS, 2000, 41 (36) : 6951 - 6954
  • [7] An efficient, rapid and highly selective preparation of the Wieland-Miescher ketone-9-ethylene ketal
    Ciceri, P
    Demnitz, FWJ
    [J]. TETRAHEDRON LETTERS, 1997, 38 (03) : 389 - 390
  • [8] CIMINO C, 1975, TETRAHEDRON LETT, P1425
  • [9] Natural sesquiterpenoids
    Fraga, BM
    [J]. NATURAL PRODUCT REPORTS, 2005, 22 (04) : 465 - 486
  • [10] TOTAL SYNTHESIS OF PALLESCENSIN-A
    GARIBOLDI, P
    JOMMI, G
    SISTI, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) : 1961 - 1962