Abstract
A key intermediate, 4-aza-3-oxo-androstane-17β-carboxylic acid, for the preparation of some potent 5α-reductase inhibitors was synthesized in 5 steps from the known methyl 3-oxo-4-androstene-17β carboxylate. The construction of 4-aza-3-oxo-ring A of the steroid was achieved conveniently by a novel one-step simultaneous lactam formation and N-debenzylation of methyl 3-(2,4-dimethoxylbenzylamine)-5-oxo- A-nor-3,4-seco-androstane-17β -carboxylate with 4 equivalents of p-TsOH.
| Original language | English |
|---|---|
| Pages (from-to) | 213-219 |
| Number of pages | 7 |
| Journal | Chinese Pharmaceutical Journal |
| Volume | 55 |
| Issue number | 3 |
| Publication status | Published - 2003 Jun 1 |
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All Science Journal Classification (ASJC) codes
- Pharmacology
- Pharmaceutical Science
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Synthesis of 4-Aza-3-oxo-androstane-17β-carboxylic Acid, a Key Intermediate for the Preparation of Potent 5α-Reductase Inhibitors. / Kan, Wai-Ming; Yek, Yung Lee; Wang, Yao Hsien; Chern, Ching Yuh.
In: Chinese Pharmaceutical Journal, Vol. 55, No. 3, 01.06.2003, p. 213-219.Research output: Contribution to journal › Article
TY - JOUR
T1 - Synthesis of 4-Aza-3-oxo-androstane-17β-carboxylic Acid, a Key Intermediate for the Preparation of Potent 5α-Reductase Inhibitors
AU - Kan, Wai-Ming
AU - Yek, Yung Lee
AU - Wang, Yao Hsien
AU - Chern, Ching Yuh
PY - 2003/6/1
Y1 - 2003/6/1
N2 - A key intermediate, 4-aza-3-oxo-androstane-17β-carboxylic acid, for the preparation of some potent 5α-reductase inhibitors was synthesized in 5 steps from the known methyl 3-oxo-4-androstene-17β carboxylate. The construction of 4-aza-3-oxo-ring A of the steroid was achieved conveniently by a novel one-step simultaneous lactam formation and N-debenzylation of methyl 3-(2,4-dimethoxylbenzylamine)-5-oxo- A-nor-3,4-seco-androstane-17β -carboxylate with 4 equivalents of p-TsOH.
AB - A key intermediate, 4-aza-3-oxo-androstane-17β-carboxylic acid, for the preparation of some potent 5α-reductase inhibitors was synthesized in 5 steps from the known methyl 3-oxo-4-androstene-17β carboxylate. The construction of 4-aza-3-oxo-ring A of the steroid was achieved conveniently by a novel one-step simultaneous lactam formation and N-debenzylation of methyl 3-(2,4-dimethoxylbenzylamine)-5-oxo- A-nor-3,4-seco-androstane-17β -carboxylate with 4 equivalents of p-TsOH.
UR - http://www.scopus.com/inward/record.url?scp=2342418009&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=2342418009&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:2342418009
VL - 55
SP - 213
EP - 219
JO - Taiwan Pharmaceutical Journal
JF - Taiwan Pharmaceutical Journal
SN - 1016-1015
IS - 3
ER -