Synthetic studies on (1S)-1-(6,7-dimethoxy-2-naphthyl)-1-(1H-imidazol-4-yl) -2-methylpropan-1-ol as a selective C17,20-lyase inhibitor

Nobuyuki Matsunaga, Tomohiro Kaku, Akio Ojida, Akihiro Tasaka

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

An asymmetric synthesis of the selective C17,20-lyase inhibitor 2 has been established in eight steps from 2,3-dihydroxynaphthalene 9. The key steps are the enantioselective oxidation of ketone 17 to the chiral α-hydroxy ketone 18 and the diastereoselective Grignard reaction of 18 to the (2R,3S)-diol 21. In addition, a simple procedure for the preparation of imidazolyl 1,4-dimagnesium bromide has been established; the Grignard reaction of 11 using this reagent in the presence of cinchonine provided 2 with 44% ee.

Original languageEnglish
Pages (from-to)2021-2028
Number of pages8
JournalTetrahedron Asymmetry
Volume15
Issue number13
DOIs
Publication statusPublished - Jul 5 2004

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Grignard reactions
Lyases
Ketones
imidazoles
ketones
inhibitors
Bromides
reagents
bromides
Oxidation
preparation
oxidation
synthesis

All Science Journal Classification (ASJC) codes

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

Cite this

Synthetic studies on (1S)-1-(6,7-dimethoxy-2-naphthyl)-1-(1H-imidazol-4-yl) -2-methylpropan-1-ol as a selective C17,20-lyase inhibitor. / Matsunaga, Nobuyuki; Kaku, Tomohiro; Ojida, Akio; Tasaka, Akihiro.

In: Tetrahedron Asymmetry, Vol. 15, No. 13, 05.07.2004, p. 2021-2028.

Research output: Contribution to journalArticle

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