Journal of the American Chemical Society

Enantioselective synthesis of stephacidin B

SB Herzon, AG Myers

Index: Herzon, Seth B.; Myers, Andrew G. Journal of the American Chemical Society, 2005 , vol. 127, # 15 p. 5342 - 5344

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Citation Number: 139

Abstract

We describe an enantioselective synthetic route to the antiproliferative alkaloid stephacidin B (1) proceeding in 18 steps and 4.0% yield from 4, 4-(ethylenedioxy)-2, 2- dimethylcyclohexanone (3). Key features of the synthetic sequence include the use of the Corey-Bakshi-Shibata (CBS) reduction to introduce asymmetry early in the synthetic route, use of the novel electrophile N-(tert-butoxycarbonyl)-5-(isopropylsulfonyloxymethyl)-2, 3- ...