TRANSFORMED STEROIDS .193. SYNTHESIS OF 16-ALPHA,17-ALPHA-ISOPROPYLIDENE DERIVATIVES OF NE-9-ALPHA,16-ALPHA,17-ALPHA,21-TETRAOL-3,20-DIONE AND ITS 17-ALPHA-THIOANALOG

Authors
TURUTA AM KAMERNITSKII AV DZHLANTIASHVILI NV KOROBOV AA VOISHVILLO NE
Citation
Am. Turuta et al., TRANSFORMED STEROIDS .193. SYNTHESIS OF 16-ALPHA,17-ALPHA-ISOPROPYLIDENE DERIVATIVES OF NE-9-ALPHA,16-ALPHA,17-ALPHA,21-TETRAOL-3,20-DIONE AND ITS 17-ALPHA-THIOANALOG, Bulletin of the Russian Academy of Sciences, Division of Chemical Sciences, 41(10), 1992, pp. 1916-1919
Citations number
13
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Russian Academy of Sciences, Division of Chemical Sciences → ACNP
ISSN journal
10635211
Volume
41
Issue
10
Year of publication
1992
Part
2
Pages
1916 - 1919
Database
ISI
SICI code
1063-5211(1992)41:10<1916:TS.SO1>2.0.ZU;2-L
Abstract
A study was carried out on the pathways for the transformation of 17al pha-epoxypregn-4-ene-9alpha,21-diol-3,20-dione to give 16alpha,17alpha -isopropylidene derivatives of 4-ene-9alpha,16alpha,17alpha,21-tetraol -3,20-dione and its 17alpha-thioanalog. The key step in this pathway i s the cis-cleavage of the 20-carboethoxyhydrazone of this epoxide by a cetic and thioacetic acids and subsequent condensation of the products formed with acetone. This pathway is an efficient approach to the syn thesis of the 16alpha,17alpha-dioxolane derivative and is equally effi cient for preparation of the thioanalog, namely, -9alpha,16alpha,21-tr iol-17alpha-thiol-3,20-dione, which has already been synthesized by an alternative method.