A very short synthesis of steroids from 1,3-butadiene and benzocyclobutenes

Authors
Michellys, PY Maurin, P Toupet, L Pellissier, H Santelli, M
Citation
Py. Michellys et al., A very short synthesis of steroids from 1,3-butadiene and benzocyclobutenes, J ORG CHEM, 66(1), 2001, pp. 115-122
Citations number
52
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
1
Year of publication
2001
Pages
115 - 122
Database
ISI
SICI code
0022-3263(20010112)66:1<115:AVSSOS>2.0.ZU;2-N
Abstract
Lewis acid mediated addition of 1,8-bis(trimethylsilyl)octa-2,6-diene (BIST RO) 1 to succinic anhydride led to spirolactone 2 [(+/-)-6,9-divinyl-1-oxas piro[4.4]nonan-2-one]. Methoxycarbonylation followed by stereoselective alk ylation by various benzocyclobutenes afforded the substituted benzocyclobut ene steroid precursors 5. Thermolysis of 5 gave rise to steroids (+/-)-6 wi th a trans-anti-cis configuration in five steps and in a highly stereoselec tive manner. Modifications of the sequence allowed the preparation of stero ids (+/-)-11 with trans-anti-trans configuration.