Stereocontrol in organic synthesis using silicon-containing compounds. A synthesis of the (±)-Prelog–Djerassi lactone

HF Chow, I Fleming

Index: Chow, Hak-Fun; Fleming, Ian Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 17 p. 2651 - 2662

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Abstract

Each of the relative stereochemical relationships present in the Prelog–Djerassi lactone 34 was set up by a stereocontrolled reaction based on the presence of a silyl group. These were the enolate protonation 3→ 4 of a β-silyl ester, the enolate alkylation 11→ 12 of a β- silyl ester, silyl-to-hydroxy conversion with r