The Journal of Organic Chemistry

Oxidation of enol silyl ethers: preparation of aeginetolide, dihydroactinidiolide, and actinidiolide

GM Rubottom, HD Juve Jr

Index: Rubottom, George M.; Juve, Henrik D. Journal of Organic Chemistry, 1983 , vol. 48, # 4 p. 422 - 425

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Citation Number: 27

Abstract

The preparation of the CI1-terpenic lactones aeginetolide (l), dihydroactinidiolide (Z), and actinidiolide (3) by using 1, 3, 3-trimethyl-2-(trimethylsiloxy) cyclohexene (9) as a common precursor is discussed. The key steps in the synthetic route involve the sequential m- chloroperbenzoic acid (MCPBA) oxidation and acetylation of 9 and of the siloxy diene 13 derived from 9.

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