Synthesis of 5 alpha-hydroxyecdysteroid analogs containing an isoxazole ring in the side chain

An analog of 5alpha-hydroxyecdysteroids having an isoxazole ring in the side chain was synthesized starting from pregnenolone through intermediate 20-hydroxy-20-(3-isopropyl-4,5-dihydroisoxazol-5-yl) derivative. alpha-Bromination of 6-oxo steroids was accompanied by elimination of the hydroxy group...

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Bibliographic Details
Published inRussian journal of organic chemistry Vol. 40; no. 10; pp. 1456 - 1461
Main Authors Litvinovskaya, RP, Drach, SV, Masalova, EN, Khripach, VA
Format Journal Article
LanguageEnglish
Published NEW YORK Springer Nature 01.10.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:An analog of 5alpha-hydroxyecdysteroids having an isoxazole ring in the side chain was synthesized starting from pregnenolone through intermediate 20-hydroxy-20-(3-isopropyl-4,5-dihydroisoxazol-5-yl) derivative. alpha-Bromination of 6-oxo steroids was accompanied by elimination of the hydroxy group from C-20 and migration of the double bond thus formed to the heteroring to afford the corresponding 20-isoxazolyl steroid.
ISSN:1070-4280
1608-3393
DOI:10.1007/s11178-005-0040-2