Synthetic studies on cytotoxic macrolides cruentarens A and B: stereoselective synthesis of the C8-C19 segment of cruentarens A and B

被引:9
作者
Prasad, Busam Ramalinga Vara [1 ]
Meshram, Harshadas Mitaram [1 ]
机构
[1] Indian Inst Chem Technol, Discovery Lab, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
关键词
CHONDROMYCES-SPECIES MYXOBACTERIA; STRUCTURE ELUCIDATION; RADICAL CYCLIZATION; DIMETHYL-SULFOXIDE; CORE STRUCTURE; OXIDATION; ALCOHOLS; SALICYLIHALAMIDE; CONSTRUCTION; BENZOLACTONE;
D O I
10.1016/j.tetasy.2010.04.068
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A stereoselective synthesis of the C-8-C-19 segment of cruentarens A and B, cytotoxic natural products, has been accomplished. The key steps involve a stereoselective radical cyclization, stereospecific methylation of a gamma, delta-epoxy acrylate, nucleophilic epoxide ring opening and a cis-Wittig olefination. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1837 / 1844
页数:8
相关论文
共 39 条
  • [1] RULES FOR RING-CLOSURE
    BALDWIN, JE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) : 734 - 736
  • [2] STEREOSELECTIVITY OF RING-CLOSURE OF SUBSTITUTED HEX-5-ENYL RADICALS
    BECKWITH, ALJ
    LAWRENCE, T
    SERELIS, AK
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (11) : 484 - 485
  • [3] SOME GUIDELINES FOR RADICAL REACTIONS
    BECKWITH, ALJ
    EASTON, CJ
    SERELIS, AK
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (11) : 482 - 483
  • [4] Total synthesis of cruentaren B
    Chakraborty, Tushar Kanti
    Chattopadhyay, Amit Kumar
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) : 3578 - 3581
  • [5] A versatile and highly selective hypervalent iodine (III)/2,2,6,6-tetramethyl-1-piperidinyloxyl-mediated oxidation of alcohols to carbonyl compounds
    DeMico, A
    Margarita, R
    Parlanti, L
    Vescovi, A
    Piancatelli, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) : 6974 - 6977
  • [6] Salicylihalamides A and B, novel cytotoxic macrolides from the marine sponge Haliclona sp.
    Erickson, KL
    Beutler, JA
    Cardellina, JH
    Boyd, MR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) : 8188 - 8192
  • [7] Concise total synthesis of cruentaren A
    Fuerstner, Alois
    Bindl, Martin
    Jean, Ludovic
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (48) : 9275 - 9278
  • [8] Simple one-pot transformations of toluene-p-sulfonates of 2,3-epoxy alcohols into allylic alcohols
    Fujii, N
    Habashita, H
    Akaji, M
    Nakai, K
    Ibuka, T
    Fujiwara, M
    Tamamura, H
    Yamamoto, Y
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (09): : 865 - 866
  • [9] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION
    GAO, Y
    HANSON, RM
    KLUNDER, JM
    KO, SY
    MASAMUNE, H
    SHARPLESS, KB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) : 5765 - 5780
  • [10] APPLICATION OF THE SWERN OXIDATION TO THE MANIPULATION OF HIGHLY REACTIVE CARBONYL-COMPOUNDS
    IRELAND, RE
    NORBECK, DW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (12) : 2198 - 2200