Synthesis of 4-Aza-3-oxo-androstane-17β-carboxylic Acid, a Key Intermediate for the Preparation of Potent 5α-Reductase Inhibitors

Wai-Ming Kan; Yung Lee Yek; Yao Hsien Wang; Ching Yuh Chern

Synthesis of 4-Aza-3-oxo-androstane-17β-carboxylic Acid, a Key Intermediate for the Preparation of Potent 5α-Reductase Inhibitors

Wai-Ming Kan, Yung Lee Yek, Yao Hsien Wang, Ching Yuh Chern

Department of Pharmacology

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

1 Citation (Scopus)

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

All Science Journal Classification (ASJC) codes

Pharmacology
Pharmaceutical Science

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title = "Synthesis of 4-Aza-3-oxo-androstane-17β-carboxylic Acid, a Key Intermediate for the Preparation of Potent 5α-Reductase Inhibitors",

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.",

author = "Wai-Ming Kan and Yek, {Yung Lee} and Wang, {Yao Hsien} and Chern, {Ching Yuh}",

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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

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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.

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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

Abstract

All Science Journal Classification (ASJC) codes

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