Novel stereoids from cetyltrimethylammonium permanganate-initiated oxidative rearrangements of 16-dehydroprogesterone

Philip R. Kym, Scott R. Wilson, William H. Gritton, John A. Katzenellenbogen

Research output: Contribution to journalArticlepeer-review

Abstract

Cetyltrimethylammonium permanganate initiates oxidative opening of the D-ring of 16-dehydroprogesterone in CH2Cl2. The novel steroids 3 and 4 have been isolated and characterized as the major products obtained from oxidative rearrangement of the steroid backbone. The X-ray crystal structure of the D-homosteroid 3 is provided, and a putative mechanism that invokes a benzilic acid rearrangement for formation of 3 is presented.

Original languageEnglish (US)
Pages (from-to)2833-2836
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number18
DOIs
StatePublished - May 2 1994

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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