Steroids and related natural products. Part XCI. Synthesis of the cardenolides canarigenin and uzarigenin

Yoshiaki Kamano, George Pettit, Machiko Tozawa

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

From 3β,14-dihydroxy-5β,14β-card-20(22)-enolide (digitoxigenin) (III), new formal total syntheses of canarigenin [3β,14-dihydroxy-14β-carda-4,20(22)-dienolide] (IIa) and uzarigenin [3β,14-dihydroxy-5α,14β-card-20(22)-enolide] (Ic) have been completed. The route found most convenient involved direct oxidation of digitoxigenin (III) with t-butyl hypochlorite to yield the 4β-chloro-3-ketone (IVb). Dehydrohalogenation to the 4-en-3-one (canarigenone) (V) was followed by selective reduction with lithium hydrido-tri-t-butoxyaluminate to afford canarigenin (IIa) and with lithium borohydride to yield uzarigenin (Ic).

Original languageEnglish (US)
Pages (from-to)1972-1976
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number19
StatePublished - 1975

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Digitoxigenin
Cardenolides
Biological Products
Steroids
Hypochlorous Acid
Ketones
Lithium
canarigenin
Oxidation

ASJC Scopus subject areas

  • Chemistry(all)
  • Medicine(all)

Cite this

Steroids and related natural products. Part XCI. Synthesis of the cardenolides canarigenin and uzarigenin. / Kamano, Yoshiaki; Pettit, George; Tozawa, Machiko.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 19, 1975, p. 1972-1976.

Research output: Contribution to journalArticle

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