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 language | English (US) |
|---|---|
| Pages (from-to) | 1972-1976 |
| Number of pages | 5 |
| Journal | Journal of the Chemical Society, Perkin Transactions 1 |
| Issue number | 19 |
| DOIs | |
| State | Published - Jan 1 1975 |
ASJC Scopus subject areas
- Chemistry(all)
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Kamano, Y., Pettit, G., & Tozawa, M. (1975). Steroids and related natural products. Part XCI. Synthesis of the cardenolides canarigenin and uzarigenin. Journal of the Chemical Society, Perkin Transactions 1, (19), 1972-1976. https://doi.org/10.1039/P19750001972