Stereocontrolled synthesis of (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2- naphthyl)-2-methylpropan-1-ol as a potent C17,20-lyase inhibitor

Akio Ojida, Nobuyuki Matsunaga, Tomohiro Kaku, Akihiro Tasaka

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

An efficient stereocontrolled synthesis of the potent C17,20- lyase inhibitor, (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2-naphthyl)-2-methyl-1- propanol 1, has been established. The stereogenic center of 1 was successfully constructed by a highly diastereoselective Grignard reaction of 2, while a subsequent imidazole ring annulation afforded 1 in an enantiomerically pure form. The procedure enables a practical synthesis of 1 that can be conveniently carried out on a multigram scale.

Original languageEnglish
Pages (from-to)1555-1559
Number of pages5
JournalTetrahedron Asymmetry
Volume15
Issue number10
DOIs
Publication statusPublished - May 24 2004

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Lyases
imidazoles
inhibitors
Grignard reactions
Propanol
synthesis
rings
imidazole
isobutyl alcohol

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Stereocontrolled synthesis of (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxy-2- naphthyl)-2-methylpropan-1-ol as a potent C17,20-lyase inhibitor. / Ojida, Akio; Matsunaga, Nobuyuki; Kaku, Tomohiro; Tasaka, Akihiro.

In: Tetrahedron Asymmetry, Vol. 15, No. 10, 24.05.2004, p. 1555-1559.

Research output: Contribution to journalArticle

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