Synthetic studies on a marine polyether toxin, gambierol:: stereoselective synthesis of the EFGH ring system via B-alkyl Suzuki coupling

被引：74

作者：

Fuwa, H ^{[1
]}

Sasaki, M ^{[1
]}

Tachibana, K ^{[1
]}

机构：

[1] Univ Tokyo, CREST, Japan Sci & Technol Corp, JST,Grad Sch Sci,Dept Chem,Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON | 2001年 / 57卷 / 15期

关键词：

marine metabolites; polyethers; Suzuki reactions; toxins;

D O I：

10.1016/S0040-4020(01)00164-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic route to the EFGH ring system (3) of gambierol (1), a marine polyether toxin isolated from the dinoflagellate Gambierdiscus toxicus, has been developed. The present synthesis features convergent coupling of the F and H rings followed by ring-closure of the G ring based on the B-alkyl Suzuki reaction of lactone-derived enol phosphates. An angular methyl group at C23 was stereoselectively introduced by treatment of sulfone 32 with trimethylaluminum. Installation of a tertiary alcohol at C21 was accomplished through stereo-selcetive dihydroxylation of exo-methylene 36 followed by selective formation of the primary p-toluensulfonate and treatment of the resultant monotosylate 40 with lithium aluminum hydride. Finally, formation of the E ring as a lactone form completed the synthesis of 3. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：3019 / 3033

页数：15

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