Issue 15, 1993

Short-step stereoselective synthesis of 2α,3α,22-triacetoxy-23,24-dinor-5α-cholan-6-one: key intermediate for the preparation of 24-norbrassinolide, dolicholide and dolichosterone

Abstract

A stereoselective synthesis of 6-oxo-23,24-dinor-5α-cholan-2α,3α,22-triyl triacetate 9 was achieved in 44% overall yield in nine steps starting from 3β-hydroxyandrost-5-en-17-one 8. The important features of this synthesis are the modified Wittig reaction on the 17-oxo steroid 8 and the stereospecific generation of the chiral centre at C-20 by a resin-catalysed ene reaction on (Z)-3β, p-tolylsulfonyloxypregna-5,17(20)-diene 11.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1993, 1819-1822

Short-step stereoselective synthesis of 2α,3α,22-triacetoxy-23,24-dinor-5α-cholan-6-one: key intermediate for the preparation of 24-norbrassinolide, dolicholide and dolichosterone

B. G. Hazra, V. S. Pore and P. L. Joshi, J. Chem. Soc., Perkin Trans. 1, 1993, 1819 DOI: 10.1039/P19930001819

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements