Amino-steroids. Part 7. The synthesis of 3α-amino-2β-hydroxy- and 2β-amino-3α-hydroxy-androst-5-en-17-one

Malcolm M Campbell; Raymond C Craig; James Redpath; David S. Savage; Thomas Sleigh

Amino-steroids. Part 7. The synthesis of 3α-amino-2β-hydroxy- and 2β-amino-3α-hydroxy-androst-5-en-17-one

Malcolm M Campbell
, Raymond C Craig
, James Redpath
, David S. Savage
, Thomas Sleigh

School of Engineering & Physical Sciences

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	3042-3047
Number of pages	6
Journal	Journal of the Chemical Society, Perkin Transactions 1
Publication status	Published - 1979

Cite this

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title = "Amino-steroids. Part 7. The synthesis of 3α-amino-2β-hydroxy- and 2β-amino-3α-hydroxy-androst-5-en-17-one",

abstract = "Stereospecific transformations of 5a6{\ss}-dichloroandrost-2-en-17- one into 3a-amino-2{\ss}-hydroxyandrost-5-en-17-one and 2{\ss}-amino-3a-hydroxyandrost-5-en-17-one have been achieved via the ?5-2{\ss},3{\ss}- and 2a,3a-epoxides. Direct treatment of the 5a,6{\ss}-dichloro-2{\ss},3{\ss}-epoxide with sodium azide gave 3a,6a-bisazido-2{\ss}-hydroxyandrost-4-en-17-one, while the 5a,6{\ss}-dichloro-2a,3a-epoxide gave 2{\ss},6a-bisazido-3a-hydroxyandrost-4-en-17-one.",

author = "Campbell, \{Malcolm M\} and Craig, \{Raymond C\} and James Redpath and Savage, \{David S.\} and Thomas Sleigh",

year = "1979",

language = "English",

pages = "3042--3047",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1472-7781",

publisher = "Chemical Society",

}

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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 - https://www.scopus.com/pages/publications/37049108443

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 -

Amino-steroids. Part 7. The synthesis of 3α-amino-2β-hydroxy- and 2β-amino-3α-hydroxy-androst-5-en-17-one

Abstract

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