Amino-steroids. Part 6. Stereospecific syntheses of eight, isomeric, steroidal vicinal 2,3-amino-alcohols

Malcolm M Campbell, Raymond C Craig, Andrew C. Boyd, Iain M. Gilbert, Robert T. Logan, James Redpath, Robert G. Roy, David S. Savage, Thomas Sleigh

Research output: Contribution to journalArticle

Abstract

The seven possible 3-amino-2-hydroxy and 2-amino-3-hydroxy isomers of the anti-arrhythmic steroid, 3a-amino-2ß-hydroxy-5a-androstan-17- one, were prepared from 5a-androst-2-en-17-one. The intermediate 2a,3a- and 2ß,3ß-epoxides and aziridines were cleaved to vicinal trans-diaxial amino- and azido-alcohols, which in turn yielded the isomers by a series of functional group inversions and transformations.

Original languageEnglish
Pages (from-to)2235-2247
Number of pages13
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1979

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Amino Alcohols
Isomers
Aziridines
Steroids
Anti-Arrhythmia Agents
Epoxy Compounds
Functional groups
Alcohols
androst-2-en-17-one
androstan-17-one

Cite this

Campbell, M. M., Craig, R. C., Boyd, A. C., Gilbert, I. M., Logan, R. T., Redpath, J., ... Sleigh, T. (1979). Amino-steroids. Part 6. Stereospecific syntheses of eight, isomeric, steroidal vicinal 2,3-amino-alcohols. Journal of the Chemical Society, Perkin Transactions 1, 2235-2247.
Campbell, Malcolm M ; Craig, Raymond C ; Boyd, Andrew C. ; Gilbert, Iain M. ; Logan, Robert T. ; Redpath, James ; Roy, Robert G. ; Savage, David S. ; Sleigh, Thomas. / Amino-steroids. Part 6. Stereospecific syntheses of eight, isomeric, steroidal vicinal 2,3-amino-alcohols. In: Journal of the Chemical Society, Perkin Transactions 1. 1979 ; pp. 2235-2247.
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abstract = "The seven possible 3-amino-2-hydroxy and 2-amino-3-hydroxy isomers of the anti-arrhythmic steroid, 3a-amino-2{\ss}-hydroxy-5a-androstan-17- one, were prepared from 5a-androst-2-en-17-one. The intermediate 2a,3a- and 2{\ss},3{\ss}-epoxides and aziridines were cleaved to vicinal trans-diaxial amino- and azido-alcohols, which in turn yielded the isomers by a series of functional group inversions and transformations.",
author = "Campbell, {Malcolm M} and Craig, {Raymond C} and Boyd, {Andrew C.} and Gilbert, {Iain M.} and Logan, {Robert T.} and James Redpath and Roy, {Robert G.} and Savage, {David S.} and Thomas Sleigh",
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Campbell, MM, Craig, RC, Boyd, AC, Gilbert, IM, Logan, RT, Redpath, J, Roy, RG, Savage, DS & Sleigh, T 1979, 'Amino-steroids. Part 6. Stereospecific syntheses of eight, isomeric, steroidal vicinal 2,3-amino-alcohols', Journal of the Chemical Society, Perkin Transactions 1, pp. 2235-2247.

Amino-steroids. Part 6. Stereospecific syntheses of eight, isomeric, steroidal vicinal 2,3-amino-alcohols. / Campbell, Malcolm M; Craig, Raymond C; Boyd, Andrew C.; Gilbert, Iain M.; Logan, Robert T.; Redpath, James; Roy, Robert G.; Savage, David S.; Sleigh, Thomas.

In: Journal of the Chemical Society, Perkin Transactions 1, 1979, p. 2235-2247.

Research output: Contribution to journalArticle

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T1 - Amino-steroids. Part 6. Stereospecific syntheses of eight, isomeric, steroidal vicinal 2,3-amino-alcohols

AU - Campbell, Malcolm M

AU - Craig, Raymond C

AU - Boyd, Andrew C.

AU - Gilbert, Iain M.

AU - Logan, Robert T.

AU - Redpath, James

AU - Roy, Robert G.

AU - Savage, David S.

AU - Sleigh, Thomas

PY - 1979

Y1 - 1979

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AB - The seven possible 3-amino-2-hydroxy and 2-amino-3-hydroxy isomers of the anti-arrhythmic steroid, 3a-amino-2ß-hydroxy-5a-androstan-17- one, were prepared from 5a-androst-2-en-17-one. The intermediate 2a,3a- and 2ß,3ß-epoxides and aziridines were cleaved to vicinal trans-diaxial amino- and azido-alcohols, which in turn yielded the isomers by a series of functional group inversions and transformations.

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EP - 2247

JO - Journal of the Chemical Society, Perkin Transactions 1

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SN - 1472-7781

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