Towards the synthesis of spongistatin 1: Diastereoselective synthesis of the C(36)-C(45) subunit

被引:29
作者
Micalizio, GC [1 ]
Roush, WR [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(99)00464-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and highly diastereoselective 12 step synthesis of the C(36)-C(45) subunit (2a) of spongistatin 1 is described. The synthesis features highly diastereoselective alpha-alkoxyallylation reactions using the gamma-alkoxy substituted allylstannanes 5 and 6, and a thermodynamically controlled intramolecular Michael addition to close the pyran, (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3351 / 3354
页数:4
相关论文
共 38 条
[1]   THE SPONGISTATINS, POTENTLY CYTOTOXIC INHIBITORS OF TUBULIN POLYMERIZATION, BIND IN A DISTINCT REGION OF THE VINCA DOMAIN [J].
BAI, RL ;
TAYLOR, GF ;
CICHACZ, ZA ;
HERALD, CL ;
KEPLER, JA ;
PETTIT, GR ;
HAMEL, E .
BIOCHEMISTRY, 1995, 34 (30) :9714-9721
[2]   HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].
BLANCHETTE, MA ;
CHOY, W ;
DAVIS, JT ;
ESSENFELD, AP ;
MASAMUNE, S ;
ROUSH, WR ;
SAKAI, T .
TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186
[3]   A method for constructing the C2-C12 dispiroacetal moiety of altohyrtin A [J].
Claffey, MM ;
Heathcock, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) :7646-7647
[4]   Synthesis of the AB spiroketal subunit of spongistatin 1 (altohyrtin A): The pyrone approach [J].
Crimmins, MT ;
Washburn, DG .
TETRAHEDRON LETTERS, 1998, 39 (41) :7487-7490
[5]   Enantioselective synthesis of altohyrtin C (spongistatin 2):: Fragment assembly and revision of the spongistatin 2 stereochemical assignment [J].
Evans, DA ;
Trotter, BW ;
Côté, B ;
Coleman, PJ ;
Dias, LC ;
Tyler, AN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) :2744-2747
[6]   Enantioselective synthesis of altohyrtin C (spongistatin 2):: Synthesis of the EF-bis(pyran) subunit [J].
Evans, DA ;
Trotter, BW ;
Côté, B ;
Coleman, PJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) :2741-2744
[7]   Enantioselective synthesis of altohyrtin C (spongistatin 2): Synthesis of the AB- and CD-spiroketal subunits [J].
Evans, DA ;
Coleman, PJ ;
Dias, LC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) :2738-2741
[8]  
Guo JS, 1998, ANGEW CHEM INT EDIT, V37, P187, DOI 10.1002/(SICI)1521-3773(19980202)37:1/2<187::AID-ANIE187>3.0.CO
[9]  
2-D
[10]   A method for constructing the C18-C28 dispiroacetal moiety of Altohyrtin A [J].
Hayes, CJ ;
Heathcock, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (09) :2678-2679