Stereospecific Preparation of Silyldienes - Electrophilic Substitution as an Access to Dienones

Patrick Le Ménez; Isabelle Berque; Valérie Fargeas; Ange Pancrazi; Marie Elise Tran Huu Dau; Janick Ardisson

doi:10.1055/s-1996-5660

Synlett 1996; 1996(11): 1125-1128
DOI: 10.1055/s-1996-5660

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Stereospecific Preparation of Silyldienes - Electrophilic Substitution as an Access to Dienones

Patrick Le Ménez, Isabelle Berque, Valérie Fargeas, Ange Pancrazi, Marie Elise Tran Huu Dau, Janick Ardisson^*

^*Laboratoire de Chimie des Substance Thérapeutiques Naturelles, associé au CNRS, BIOCIS, Centre d’Etudes Pharmaceutiques 92296, Châtenay-Malabry, France

Abstract

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Substituted trimethylsilyldienes 12a-14a were prepared in high yield and total stereocontrol using a metallate rearrangement induced by the reaction of the dilithiumbis-[(E)-2-(trimethylsilyl)ethenyl]cyanocuprate 11 with the 5-lithio-2,3-dihydrofuran 7-9. Trimethylsilyldienes 12-14 were then submitted to an electrophilic substitution in the presence of acetyl chloride and aluminium trichloride for an access to the corresponding dienones 15-22. Results were tentatively explained with the aid of a modeling study.

Metallate rearrangement - silyldiene - electrophilic substitution - dienone - synthesis - tylosin - des-epoxy-rosaramycin

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