Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 66, Issue 1, Pages 115-122Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo001106f
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Lewis acid mediated addition of 1,8-bis(trimethylsilyl)octa-2,6-diene (BISTRO) 1 to succinic anhydride led to spirolactone 2 [(+/-)-6,9-divinyl-1-oxaspiro[4.4]nonan-2-one]. Methoxycarbonylation followed by stereoselective alkylation by various benzocyclobutenes afforded the substituted benzocyclobutene steroid precursors 5. Thermolysis of 5 gave rise to steroids (+/-)-6 with a trans-anti-cis configuration in five steps and in a highly stereoselective manner. Modifications of the sequence allowed the preparation of steroids (+/-)-11 with trans-anti-trans configuration.
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