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
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 [J].
BREEN, AP ;
MURPHY, JA ;
PATTERSON, CW ;
WOOSTER, NF .
TETRAHEDRON, 1993, 49 (46) :10643-10654
[3]   IMPROVED PROCEDURE FOR THE SYNTHESIS OF ENANTIOMERICALLY ENRICHED CYCLOPROPYLMETHANOL DERIVATIVES [J].
CHARETTE, AB ;
PRESCOTT, S ;
BROCHU, C .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) :1081-1083
[4]   FORMATION OF OXAZOLINES AND THIAZOLINES IN PEPTIDES BY THE MITSUNOBU REACTION [J].
GALEOTTI, N ;
MONTAGNE, C ;
PONCET, J ;
JOUIN, P .
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 [J].
GERWICK, WH ;
PROTEAU, PJ ;
NAGLE, DG ;
HAMEL, E ;
BLOKHIN, A ;
SLATE, DL .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (06) :1243-1245
[6]   Total synthesis of curacin A [J].
Hoemann, MZ ;
Agrios, KA ;
Aube, 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 [J].
Ito, H ;
Imai, N ;
Takao, K ;
Kobayashi, S .
TETRAHEDRON LETTERS, 1996, 37 (11) :1799-1800
[8]   Enantioselective synthesis of curacin A .1. Construction of C1-C7, C8-C17, and C18-C22 segments [J].
Ito, H ;
Imai, N ;
Tanikawa, S ;
Kobayashi, S .
TETRAHEDRON LETTERS, 1996, 37 (11) :1795-1798
[9]   CATALYTIC ASYMMETRIC ALLYLATION OF ALDEHYDES [J].
KECK, GE ;
TARBET, KH ;
GERACI, LS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) :8467-8468
[10]   2-CARBON ELONGATION/ANNULATION OF ALCOHOLS TO NITRILES [J].
LAI, JY ;
YU, JR ;
HAWKINS, RD ;
FALCK, JR .
TETRAHEDRON LETTERS, 1995, 36 (32) :5691-5694