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
Externally publishedYes

All Science Journal Classification (ASJC) codes

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

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