Issue 47, 2012
From the journal:

Chemical Communications

Convenient method for the functionalization of the 4- and 6-positions of the androgen skeleton†

Daniel Morton,a   Allison R. Dick,b   Debashis Ghoshc  and  Huw M. L. Davies*a  

* Corresponding authors

a Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, GA, USA
E-mail: hmdavie@emory.edu
Tel: 001 404 727 6839

b Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, USA

c Pharmacology and Upstate Cancer Research Institute, SUNY Upstate Medical University, Room 6310, Weiskotten Hall, 750 East Adams Street, Syracuse, USA

Abstract

The preparation and reactivity of steroidal vinyldiazo compounds is reported, providing a convenient, substituent tolerant, chemo- and stereoselective entry into 4- and 6-substituted androgen analogues from a common precursor. Under dirhodium catalysis, O–H insertion occurs at the carbenoid site, leading to 4-substituted steroids, but under silver catalysis, O–H insertion occurs at the vinylogous position, leading to 6-substituted steroids.

Graphical abstract: Convenient method for the functionalization of the 4- and 6-positions of the androgen skeleton

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Article information

DOI
https://doi.org/10.1039/C2CC31973J
Article type
Communication
Submitted
18 Mar 2012
Accepted
20 Apr 2012
First published
24 Apr 2012

Chem. Commun., 2012,48, 5838-5840

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Convenient method for the functionalization of the 4- and 6-positions of the androgen skeleton

D. Morton, A. R. Dick, D. Ghosh and H. M. L. Davies, Chem. Commun., 2012, 48, 5838 DOI: 10.1039/C2CC31973J

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