Issue 3, 2015

Formation of the steroidal C-25 chiral center via the asymmetric alkylation methodology

Abstract

A novel approach for the preparation of steroids containing a chiral center at C-25 is reported. The key stereochemistry inducing step was asymmetric alkylation of pseudoephenamine amides of steroidal C-26 acids. The reaction proceeded with high diastereoselectivity (dr > 99 : 1). The developed methodology was successfully applied to the synthesis of (25R)- and (25S)-cholestenoic acids as well as (25R)- and (25S)-26-hydroxy brassinolides.

Graphical abstract: Formation of the steroidal C-25 chiral center via the asymmetric alkylation methodology

Supplementary files

Article information

Article type
Paper
Submitted
05 Oct 2014
Accepted
03 Nov 2014
First published
03 Nov 2014

Org. Biomol. Chem., 2015,13, 776-782

Author version available

Formation of the steroidal C-25 chiral center via the asymmetric alkylation methodology

Yu. V. Ermolovich, V. N. Zhabinskii and V. A. Khripach, Org. Biomol. Chem., 2015, 13, 776 DOI: 10.1039/C4OB02123A

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