SYNTHESIS OF (19E)-3-BETA,17-DIHYDROXY-20-OXOPREGN-5-EN-19-AL 19-(O-CARBOXYMETHYL)OXIME, NEW STEROIDAL HAPTEN FOR 17-HYDROXYPREGNENOLONE

Authors
POUZAR V FAJKOS J
Citation
V. Pouzar et J. Fajkos, SYNTHESIS OF (19E)-3-BETA,17-DIHYDROXY-20-OXOPREGN-5-EN-19-AL 19-(O-CARBOXYMETHYL)OXIME, NEW STEROIDAL HAPTEN FOR 17-HYDROXYPREGNENOLONE, Steroids, 59(12), 1994, pp. 696-701
Citations number
10
Categorie Soggetti
Biology,"Endocrynology & Metabolism
Journal title
Steroids → ACNP
ISSN journal
0039128X
Volume
59
Issue
12
Year of publication
1994
Pages
696 - 701
Database
ISI
SICI code
0039-128X(1994)59:12<696:SO(1>2.0.ZU;2-8
Abstract
A synthesis of (19E)-3 beta,17-dihydroxy-20-oxopregn-5-en-19-al 19-(O- carboxymethyl)oxime (15), is reported Hydride reduction of ketone 1 ga ve the (20R)-hydroxy derivative 2 as the main product. Formylation of 2 followed by cleavage of the epoxide ring and mild Jones oxidation af forded aldehyde 6. Oximation with (O-carboxymethyl)hydroxylamine and s ubsequent methylation yielded methyl ester 8 which was selectively hyd rolyzed to alcohol 9 and oxidized to ketone 10. Enolacetylation, epoxi dation, and hydrolysis led to the desired 19-(O-carboxymethyl) oxime d erivative of 17-hydroxypregnenolone 15.