A simple chemical method for synthesizing malonyl hemiesters of 21-hydroxypregnanes, potential intermediates in cardenolide biosynthesis.
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.
Pádua
Rodrigo M
RM
Friedrich-Alexander-Universität, Lehrstuhl für Pharmazeutische Biologie, Staudtstr. 5, D-91058 Erlangen, Germany.
Waibel
Reiner
R
Kuate
Serge Philibert
SP
Schebitz
Pia K
PK
Hahn
Stefanie
S
Gmeiner
Peter
P
Kreis
Wolfgang
W
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000737:chemistry; D002298:Cardenolides / Q000138:chemical synthesis* / Q000737:chemistry*; D004073:Digitoxigenin / Q000737:chemistry; D004952:Esters; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D011278:Pregnanes / Q000737:chemistry*; D011284:Pregnenolone / Q000737:chemistry*
D002298:Cardenolides; D004952:Esters; D011278:Pregnanes; D004073:Digitoxigenin; D011284:Pregnenolone; C004511:butenolide; D015107:4-Butyrolactone