A synthesis of C-23 and C-24 diastereomers of 5α-dinosterane

Ivan Stoilov, Ewa Kolaczkowska, Jan St Pyrek, Carolyn P. Brock, David S. Watt, R. M.K. Carlson, J. Michael Moldowan

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Stereoselective routes for the preparation of C-23 and C-24 diastereomers of the C30 biological marker, 5α-dinosterane (1), involved the alkylation of (20S)-20-(iodomethyl)-4α-methyl-5α-pregnane (7) with either a saturated ester, methyl 3,4-dimethylpentanoate (9), followed by reduction to give principally the erythro-diastereomers or the alkylation of 7 with an α,β-unsaturated ester, methyl 3,4-dimethylpentenoate (12), followed by reduction to give principally the threo-diastereomers.

Original languageEnglish
Pages (from-to)7689-7692
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number50
DOIs
StatePublished - Dec 8 1993

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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