Selective epoxidation of
the methoxy alkene mixture (IX) from oxidative decarboxylation of
12-methoxypodocarpa-8,11,13-trien-19-oic acid (I)
provides a method of obtaining a high yield of the exocyclic alkene (VII) from
the mixture. Isolation of the 3α,4α-epoxide
(X) during the epoxidation allows the formation of C 3 oxygenated derivatives
of 12- methoxypodocarpa-8,11,13-trien-19-oic acid. ��� Methods for opening the epoxide ring of (X)
and of the 4α,5α- and 4α,19-epoxides,
(XI) and (XII), have been examined, and the structures of the products from
rearrangement of each epoxide with boron trifluoride have been assigned.
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