A highly efficient, stereoselective oxyfunctionalization of unactivated carbons in steroids with dimethyldioxirane

T. Iida, T. Yamaguchi, R. Nakamori, M. Hikosaka, Nariyasu Mano, J. Gotob, T. Nambarac

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

Oxyfunctionalization of unactivated methine carbon atoms with dimethyldioxirane (DMDO) is studied for various substituted steroids related to the 5β-cholane and 5α-cholestane series. A highly efficient, stereoselective, one-step remote oxidation of specific methine carbons is attained by DMDO oxidation under mild conditions to give a variety of novel mono- and dihydroxylated steroids. The reactivity and site selectivity of remote oxyfunctionalization is influenced significantly by the structural and steric environments as well as by the degree of electron density of the target methine carbon atoms in the molecules. The non-enzymatic procedure may be usefully applied to effective and short-step syntheses of bioactive steroids.

Original languageEnglish
Pages (from-to)2229-2236
Number of pages8
JournalJournal of the Chemical Society. Perkin Transactions 1
Issue number18
DOIs
Publication statusPublished - 2001 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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