TY - JOUR
T1 - Amino-steroids. Part 7. The synthesis of 3α-amino-2β-hydroxy- and 2β-amino-3α-hydroxy-androst-5-en-17-one
AU - Campbell, Malcolm M
AU - Craig, Raymond C
AU - Redpath, James
AU - Savage, David S.
AU - Sleigh, Thomas
PY - 1979
Y1 - 1979
N2 - Stereospecific transformations of 5a6ß-dichloroandrost-2-en-17- one into 3a-amino-2ß-hydroxyandrost-5-en-17-one and 2ß-amino-3a-hydroxyandrost-5-en-17-one have been achieved via the ?5-2ß,3ß- and 2a,3a-epoxides. Direct treatment of the 5a,6ß-dichloro-2ß,3ß-epoxide with sodium azide gave 3a,6a-bisazido-2ß-hydroxyandrost-4-en-17-one, while the 5a,6ß-dichloro-2a,3a-epoxide gave 2ß,6a-bisazido-3a-hydroxyandrost-4-en-17-one.
AB - Stereospecific transformations of 5a6ß-dichloroandrost-2-en-17- one into 3a-amino-2ß-hydroxyandrost-5-en-17-one and 2ß-amino-3a-hydroxyandrost-5-en-17-one have been achieved via the ?5-2ß,3ß- and 2a,3a-epoxides. Direct treatment of the 5a,6ß-dichloro-2ß,3ß-epoxide with sodium azide gave 3a,6a-bisazido-2ß-hydroxyandrost-4-en-17-one, while the 5a,6ß-dichloro-2a,3a-epoxide gave 2ß,6a-bisazido-3a-hydroxyandrost-4-en-17-one.
UR - http://www.scopus.com/inward/record.url?scp=37049108443&partnerID=8YFLogxK
M3 - Article
SN - 1472-7781
SP - 3042
EP - 3047
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
ER -