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 language||English (US)|
|Number of pages||3|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|State||Published - 1975|
ASJC Scopus subject areas