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  • A simple chemical method for synthesizing malonyl hemiesters of 21-hydroxypregnanes, potential intermediates in cardenolide biosynthesis.

A simple chemical method for synthesizing malonyl hemiesters of 21-hydroxypregnanes, potential intermediates in cardenolide biosynthesis.

Steroids (2008-02-06)
Rodrigo M Pádua, Reiner Waibel, Serge Philibert Kuate, Pia K Schebitz, Stefanie Hahn, Peter Gmeiner, Wolfgang Kreis
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 beta-methyldigitoxin, acid hydrolysis followed by 3beta-O-acetylation and ozonolysis with reductive cleavage of the ozonides afforded 3beta-acetoxy-5beta-pregnane-14beta,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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Sigma-Aldrich
Digitoxigenin