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J Org Chem. 2004 Feb 6;69(3):832-8.

Novel synthesis of highly functionalized 14-beta-hydroxysteroids related to batrachotoxin and ouabain.

Author information

1
Laboratoire de synthèse organique, Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, Sherbrooke, Québec J1H 5N4, Canada.

Abstract

The use of anionic polycyclization was investigated in an effort to develop a versatile and convergent synthesis of advanced tetracyclic intermediates of batrachotoxin and ouabain analogues. Two new 5-(trialkylsilyl)-2-cyclohexenones as A ring precursors and a new Nazarov intermediate (D ring precursor) were prepared for this purpose. The reaction of the unsaturated beta-keto aldehyde A ring precursor with the enolate of the Nazarov intermediate afforded, after subsequent transformations, a 14-beta-hydroxysteroid with complete control of stereochemistry.

PMID:
14750812
DOI:
10.1021/jo0355606
[Indexed for MEDLINE]

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