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)|
|Number of pages||5|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|State||Published - 1975|
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