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Synthesis 1992; 1992(9): 833-834
DOI: 10.1055/s-1992-26238
short paper
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Allylically Stannylated Cholestenes: The Synthesis of 3α-(Triphenylstannyl)cholest-4-ene, 7α-(Tributylstannyl)- and 7α-(Triphenylstannyl)cholest-5-en-3-one, and 7α-(Triphenylstannyl)-cholest-5-en-3β-ol

Hai-Shan Dang* , Alwyn G. Davies
  • *Chemistry Department, University College London, 20 Gordon Street, London WC1H OAJ, England
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Publication Date:
17 September 2002 (online)

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3α-(Triphenylstannyl)cholest-4-ene can be prepared by the reaction of triphenylstannyllithium with 3-chlorocholest-4-ene. Cholesta-4,6-dien-3-one reacts with tributylstannyllithium, lithium bis(triphenylstannyl)cuprate or triphenylstannyllithium to give the corresponding 7α-(triorganostannyl)cholest-5-en-3-one, and the triphenylstannyl derivative can be reduced with lithium aluminium hydride to give 7α-(triphenylstannyl) cholest-5-en-3β-ol.