Synthesis of curacin A, an antimitotic cyclopropane-thiazoline from the marine cyanobacterium Lyngbya majuscula

被引：64
作者：
Lai, JY
Yu, JR
Mekonnen, B
Falck, JR
机构：
[1] UNIV TEXAS,SW MED CTR,DEPT BIOCHEM,DALLAS,TX 75235
[2] UNIV TEXAS,SW MED CTR,DEPT PHARMACOL,DALLAS,TX 75235
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 40期
关键词：
D O I：
10.1016/0040-4039(96)01616-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Charette asymmetric cyclopropanation, chiral thiazoline synthesis by thioamide cyclization under modified Mitsunobu conditions, Ti(iPrO)(4)/bi-naphthol catalyzed allylstannane addition, and an exceptionally mild two-carbon homologation via dehydrative alkylation with phenylsulfonylacetonitrile/Ph(3)P/ADDP convened in an efficient, stereocontrolled route to the title bioactive heterocycle. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码：7167 / 7170
页数：4
相关论文
共 18 条
  • [1] BLOKHIN AV, 1995, MOL PHARMACOL, V48, P523
  • [2] RADICAL-INDUCED FRAGMENTATIONS OF KETOEPOXIDES
    BREEN, AP
    MURPHY, JA
    PATTERSON, CW
    WOOSTER, NF
    [J]. TETRAHEDRON, 1993, 49 (46) : 10643 - 10654
  • [3] IMPROVED PROCEDURE FOR THE SYNTHESIS OF ENANTIOMERICALLY ENRICHED CYCLOPROPYLMETHANOL DERIVATIVES
    CHARETTE, AB
    PRESCOTT, S
    BROCHU, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) : 1081 - 1083
  • [4] FORMATION OF OXAZOLINES AND THIAZOLINES IN PEPTIDES BY THE MITSUNOBU REACTION
    GALEOTTI, N
    MONTAGNE, C
    PONCET, J
    JOUIN, P
    [J]. TETRAHEDRON LETTERS, 1992, 33 (20) : 2807 - 2810
  • [5] STRUCTURE OF CURACIN-A, A NOVEL ANTIMITOTIC, ANTIPROLIFERATIVE, AND BRINE SHRIMP TOXIC NATURAL PRODUCT FROM THE MARINE CYANOBACTERIUM LYNGBYA-MAJUSCULA
    GERWICK, WH
    PROTEAU, PJ
    NAGLE, DG
    HAMEL, E
    BLOKHIN, A
    SLATE, DL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (06) : 1243 - 1245
  • [6] Total synthesis of curacin A
    Hoemann, MZ
    Agrios, KA
    Aube, J
    [J]. TETRAHEDRON LETTERS, 1996, 37 (07) : 953 - 956
  • [7] Enantioselective synthesis of curacin A .2. Total synthesis of curacin A by condensation of C1-C7, CS-C14, and C18-C22 segments
    Ito, H
    Imai, N
    Takao, K
    Kobayashi, S
    [J]. TETRAHEDRON LETTERS, 1996, 37 (11) : 1799 - 1800
  • [8] Enantioselective synthesis of curacin A .1. Construction of C1-C7, C8-C17, and C18-C22 segments
    Ito, H
    Imai, N
    Tanikawa, S
    Kobayashi, S
    [J]. TETRAHEDRON LETTERS, 1996, 37 (11) : 1795 - 1798
  • [9] CATALYTIC ASYMMETRIC ALLYLATION OF ALDEHYDES
    KECK, GE
    TARBET, KH
    GERACI, LS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) : 8467 - 8468
  • [10] 2-CARBON ELONGATION/ANNULATION OF ALCOHOLS TO NITRILES
    LAI, JY
    YU, JR
    HAWKINS, RD
    FALCK, JR
    [J]. TETRAHEDRON LETTERS, 1995, 36 (32) : 5691 - 5694
12