A Very Short Synthesis of Steroids from 1,3-Butadiene and Benzocyclobutenes

• DOI: 10.1021/jo001106f
• Publication Date: 2002-07-26T04:53:54Z
• Authors: Pierre-Yves Miche...; Philippe Maurin; Loïc Toupet; Hélène Pellissier; Maurice Santelli
• Keywords: Succinic anhydride; Benzocyclobutene; Trimethylsilyl; Diene

Lewis acid mediated addition of 1,8-bis(trimethylsilyl)octa-2,6-diene (BISTRO) 1 to succinic anhydride led spirolactone 2 [(±)-6,9-divinyl-1-oxaspiro[4.4]nonan-2-one]. Methoxycarbonylation followed by stereoselective alkylation various benzocyclobutenes afforded the substituted benzocyclobutene steroid precursors 5. Thermolysis 5 gave rise steroids (±)-6 with a trans-anti-cis configuration in five steps and highly manner. Modifications sequence allowed preparation (±)-11 trans-anti-trans configuration.