Synthesis of a C, D-ring fragment of artemisinin

…, C Jennings-White, WKM Chong

Index: Avery, Mitchell A.; Jennings-White, Clive; Chong, Wesley K. M. Journal of Organic Chemistry, 1989 , vol. 54, # 8 p. 1789 - 1792

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Citation Number: 30

Abstract

A multistep preparation is described for carboxyvinylsilane 6, which upon reaction with ozone initially gave dioxetane 8 as a transient intermediate in a highly stereoselective manner. Subsequent rearrangement at ambient temperature resulted in cyclization to (*)- hexahydroisochroman-3-one 2, whose relative stereochemistry was determined by X-ray crystallographic analysis and found to resemble the C, D-ring portion of the antimalarial ...

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