Synthetic uses of steroidal ring B diene protection: 22,23-dihydroergosterol

Derek H.R. Barton, A. A.Leslie Gunatilaka, Tsutomu Nakanishi, Henri Patin, David A. Widdowson, Brian R. Worth

Research output: Contribution to journalArticlepeer-review

72 Scopus citations

Abstract

Protection of the ring B diene system of ergosterol by (i) a two-step addition of the elements of water across the 5,6-double bond, (ii) formation of the 4-phenyl-1,2,4-triazoline-3,5-dione adduct, or (iii) formation of the iron tricarbonyl adduct by treatment with p-methoxybenzylideneacetonetricarbonyliron, allowed selective reduction of the 22,23-double bond by catalytic or, as appropriate, ionic hydrogenation. Regeneration of the 5,7-diene system in each case gave a high yield of 22,23-dihydroergosterol.

Original languageEnglish (US)
Pages (from-to)821-826
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number8
DOIs
StatePublished - Jan 1 1976
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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