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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)213-219
Number of pages7
JournalChinese Pharmaceutical Journal
Volume55
Issue number3
Publication statusPublished - 2003 Jun 1

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Androstenes
Lactams
Oxidoreductases
Steroids
androstane
etianic acid

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Pharmaceutical Science

Cite this

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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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pages = "213--219",
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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 journalArticle

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