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

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 benzocyclobuten...

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Bibliographic Details
Published in:Journal of organic chemistry 2001-01, Vol.66 (1), p.115-122
Main Authors: Michellys, Pierre-Yves, Maurin, Philippe, Toupet, Loïc, Pellissier, Hélène, Santelli, Maurice
Format: Article
Language:English
Subjects:
Alkylation
Butadienes - chemistry
Crystallography, X-Ray
Indicators and Reagents
Magnetic Resonance Spectroscopy
Molecular Conformation
Polycyclic Compounds - chemistry
Spironolactone - chemical synthesis
Stereoisomerism
Steroids - chemical synthesis
Steroids - chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo001106f