TY - JOUR
T1 - Inhibitors of Steroid Biosynthesis
T2 - Preparation of 5,10-Secoestr-4-ynes
AU - Covey, Douglas F.
AU - Parikh, Vinod D.
PY - 1982/1/1
Y1 - 1982/1/1
N2 - This paper describes two novel syntheses of 5,10-secoestr-4-yne-3,10,17-trione, a compound which has been shown previously to be a powerful irreversible inhibitor of both bacterial and mammalian Δ5-3-keto steroid isomerases. One synthetic route makes available 3β-hydroxy-4-acetylenic 5,10-seco steroids and the other provides 3α-hydroxy-4-acetylenic 5,10-seco steroids. Stereospecific routes to these epimeric α,β-acetylenic alcohols were developed because of their potential utility as mechanism-based inhibitors of the corresponding 3α- and 3β-hydroxy steroid dehydrogenases.
AB - This paper describes two novel syntheses of 5,10-secoestr-4-yne-3,10,17-trione, a compound which has been shown previously to be a powerful irreversible inhibitor of both bacterial and mammalian Δ5-3-keto steroid isomerases. One synthetic route makes available 3β-hydroxy-4-acetylenic 5,10-seco steroids and the other provides 3α-hydroxy-4-acetylenic 5,10-seco steroids. Stereospecific routes to these epimeric α,β-acetylenic alcohols were developed because of their potential utility as mechanism-based inhibitors of the corresponding 3α- and 3β-hydroxy steroid dehydrogenases.
UR - http://www.scopus.com/inward/record.url?scp=0020442345&partnerID=8YFLogxK
U2 - 10.1021/jo00148a017
DO - 10.1021/jo00148a017
M3 - Article
AN - SCOPUS:0020442345
SN - 0022-3263
VL - 47
SP - 5315
EP - 5318
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 27
ER -