ONE-POT DEUTERATION AND REDUCTION OF KETONES IN THE SYNTHESIS OF [16,16,17-H-2(3)]-EPITESTOSTERONE

Authors
CHODOUNSKA H KASAL A SAMAN D UBIK K
Citation
H. Chodounska et al., ONE-POT DEUTERATION AND REDUCTION OF KETONES IN THE SYNTHESIS OF [16,16,17-H-2(3)]-EPITESTOSTERONE, Collection of Czechoslovak Chemical Communications, 61(7), 1996, pp. 1037-1046
Citations number
27
Categorie Soggetti
Chemistry
Journal title
Collection of Czechoslovak Chemical Communications → ACNP
ISSN journal
00100765
Volume
61
Issue
7
Year of publication
1996
Pages
1037 - 1046
Database
ISI
SICI code
0010-0765(1996)61:7<1037:ODAROK>2.0.ZU;2-J
Abstract
5 alpha-Androstan-17-one and 6 beta-methoxy-3 alpha,5-cyclo-5 alpha-an drostan-17-one were reduced by sodium in deuterium oxide to [16,16,17- H-2(3)]-17 beta-alcohols. The 17 beta-tosyloxy group of [16,16,17-H-2( 3)]-6 beta-methoxy-3 alpha,5-cyclo-5 alpha-androstan-17 beta-ol tosyla te was found to be stable under the conditions of the i-steroid rearra ngement. The S(N)2 reaction of the 17 beta-tosyloxy group with potassi um nitrite yielded the corresponding 17 alpha-hydroxy derivative witho ut any loss of deuterium.