Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
2029508 | Steroids | 2008 | 8 Pages |
Abstract
A simple and versatile method for the chemical synthesis of 21-hydroxypregnane 21-O-malonyl hemiesters which may be important intermediates of cardenolide biosynthesis is described. Starting from commercial β-methyldigitoxin, acid hydrolysis followed by 3β-O-acetylation and ozonolysis with reductive cleavage of the ozonides afforded 3β-acetoxy-5β-pregnane-14β,21-diol-20-one which was finally converted into the target compound by treatment with malonyl chloride. The malonylation protocol was optimized using deoxycorticosterone (DOC) as the pregnane educt.
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Authors
Rodrigo M. Pádua, Reiner Waibel, Serge Philibert Kuate, Pia K. Schebitz, Stefanie Hahn, Peter Gmeiner, Wolfgang Kreis,