期刊
TETRAHEDRON
卷 57, 期 15, 页码 3019-3033出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)00164-8
关键词
marine metabolites; polyethers; Suzuki reactions; toxins
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.
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