Synthesis of 3α-hydroxy-21-(1′-imidazolyl)-3β-methoxyl- methyl-5α-pregnan-20-one via lithium imidazole with 17α- acetylbromopregnanone

Fung Fuh Wong, Chun-Yen Chen, Tse Hsin Chen, Jiann Jyh Huang, Hsiao Ping Fang, Mou Yung Yeh

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

The synthesis of biologically active 3α-hydroxyl-21-(1′- imidazolyl)-3β-methoxymethyl-5α-pregnan-20-one (11) was accomplished in six steps. The key steps were the improvement of stereoselectivity for acetyl isomers in C-17 and the introduction of imidazole into the core structure by use of lithium imidazole. This latter key step provided the desired product 11 in 82% yield without the formation of 1,3-disubstituted imidazolium salt as impurity, which is generally observed in traditional method.

Original languageEnglish
Pages (from-to)77-82
Number of pages6
JournalSteroids
Volume71
Issue number1
DOIs
Publication statusPublished - 2006 Jan 1

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Lithium
Stereoselectivity
Isomers
Hydroxyl Radical
Salts
Impurities
imidazole
pregnane-20-one

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Endocrinology
  • Pharmacology
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Wong, Fung Fuh ; Chen, Chun-Yen ; Chen, Tse Hsin ; Huang, Jiann Jyh ; Fang, Hsiao Ping ; Yeh, Mou Yung. / Synthesis of 3α-hydroxy-21-(1′-imidazolyl)-3β-methoxyl- methyl-5α-pregnan-20-one via lithium imidazole with 17α- acetylbromopregnanone. In: Steroids. 2006 ; Vol. 71, No. 1. pp. 77-82.
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abstract = "The synthesis of biologically active 3α-hydroxyl-21-(1′- imidazolyl)-3β-methoxymethyl-5α-pregnan-20-one (11) was accomplished in six steps. The key steps were the improvement of stereoselectivity for acetyl isomers in C-17 and the introduction of imidazole into the core structure by use of lithium imidazole. This latter key step provided the desired product 11 in 82{\%} yield without the formation of 1,3-disubstituted imidazolium salt as impurity, which is generally observed in traditional method.",
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Synthesis of 3α-hydroxy-21-(1′-imidazolyl)-3β-methoxyl- methyl-5α-pregnan-20-one via lithium imidazole with 17α- acetylbromopregnanone. / Wong, Fung Fuh; Chen, Chun-Yen; Chen, Tse Hsin; Huang, Jiann Jyh; Fang, Hsiao Ping; Yeh, Mou Yung.

In: Steroids, Vol. 71, No. 1, 01.01.2006, p. 77-82.

Research output: Contribution to journalArticle

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AB - The synthesis of biologically active 3α-hydroxyl-21-(1′- imidazolyl)-3β-methoxymethyl-5α-pregnan-20-one (11) was accomplished in six steps. The key steps were the improvement of stereoselectivity for acetyl isomers in C-17 and the introduction of imidazole into the core structure by use of lithium imidazole. This latter key step provided the desired product 11 in 82% yield without the formation of 1,3-disubstituted imidazolium salt as impurity, which is generally observed in traditional method.

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