Steroids and related natural products. Part XCII. Conversion of canarigenone[14-hydroxy-3-oxo-14β-carda-4,20(22)-dienolide] into periplogenin [3β,5,14-trihydroxy-5β,14β-card-20(22)-enolide]

Yoshiaki Kamano, George Pettit, Machiko Tozawa

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

Oxidation of canarigenone (IV) by peroxy-acid gave the 4β,5β-epoxide (V), which was reduced by chromium(II) acetate to the 5β-hydroxy-3-ketone (VI). Selective reduction of this with Urushibara nickel A led to periplogenin (Ia). The epoxy-ketone (V) was also prepared from canarigenin (VII). Since digitoxigenin (III) had previously been converted to canarigenin (VII) and canarigenone (VI) the synthetic route to periplogenin constituted a formal total synthesis.

Original languageEnglish (US)
Pages (from-to)1976-1978
Number of pages3
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number19
DOIs
StatePublished - Jan 1 1975

ASJC Scopus subject areas

  • Chemistry(all)

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