Synthesis and transformations of 2 beta,3 beta-diacetoxy-20-(4,5-dihydroisoxazol-5-yl)-6-oxo steroids

20-Hydroxy-20-(4,5-dihydroisoxazol-5-yl) steroid was brought into reactions typical of functionalization of rings A and B in ecdysteroids. The dihydroisoxazole ring remained unchanged in reactions leading to formation of the 2beta,3beta-dihydroxy-6-oxo moiety. The isomerization of 5alpha-bromo deriv...

Full description

Saved in:
Bibliographic Details
Published inRussian journal of organic chemistry Vol. 40; no. 10; pp. 1450 - 1455
Main Authors Litvinovskaya, RP, Drach, SV, Khripach, VA
Format Journal Article
LanguageEnglish
Published NEW YORK Springer Nature 01.10.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SIDE-CHAIN
Online AccessGet full text

Cover

More Information
Summary:20-Hydroxy-20-(4,5-dihydroisoxazol-5-yl) steroid was brought into reactions typical of functionalization of rings A and B in ecdysteroids. The dihydroisoxazole ring remained unchanged in reactions leading to formation of the 2beta,3beta-dihydroxy-6-oxo moiety. The isomerization of 5alpha-bromo derivative in acetic acid in the presence of a catalytic amount of hydrobromic acid and Lewis acids is accompanied by elimination of the hydroxy group from C-20 and subsequent migration of the double bond to the heteroring to afford the corresponding isoxazole derivative.
ISSN:1070-4280
1608-3393
DOI:10.1007/s11178-005-0039-8