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Updated: Apr 21, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Formation of the steroidal C-25 chiral center via the asymmetric alkylation methodology
Yu V Ermolovich1, V N Zhabinskii, V A Khripach
1Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich st., 5/2, 220141 Minsk, Belarus. vz@iboch.bas-net.by.
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.
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