Synthetic uses of steroidal ring B diene protection

22,23- dihydroergosterol

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

Research output: Contribution to journalArticle

71 Citations (Scopus)

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
StatePublished - 1976
Externally publishedYes

Fingerprint

Ergosterol
Hydrogenation
Regeneration
Iron
Water
22,23-dihydroergosterol
4-phenyl-1,2,4-triazoline-3,5-dione

ASJC Scopus subject areas

  • Chemistry(all)
  • Medicine(all)

Cite this

Barton, D. H. R., Gunatilaka, L., Nakanishi, T., Patin, H., Widdowson, D. A., & Worth, B. R. (1976). Synthetic uses of steroidal ring B diene protection: 22,23- dihydroergosterol. Journal of the Chemical Society, Perkin Transactions 1, (8), 821-826.

Synthetic uses of steroidal ring B diene protection : 22,23- dihydroergosterol. / Barton, Derek H R; Gunatilaka, Leslie; Nakanishi, Tsutomu; Patin, Henri; Widdowson, David A.; Worth, Brian R.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 8, 1976, p. 821-826.

Research output: Contribution to journalArticle

Barton, Derek H R ; Gunatilaka, Leslie ; Nakanishi, Tsutomu ; Patin, Henri ; Widdowson, David A. ; Worth, Brian R. / Synthetic uses of steroidal ring B diene protection : 22,23- dihydroergosterol. In: Journal of the Chemical Society, Perkin Transactions 1. 1976 ; No. 8. pp. 821-826.
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