The synthesis and ozonolysis of the 6- and 7-substituted 12-hydroxypodocarpatrienes (26), (86), (90), and (98), as a possible route for the synthesis of drimanes from 12-hydroxypodocarpa-8,11,13-trien-19-oic acid (podocarpic acid) (9) has been investigated. Modification of the aromatic ring of (9) has given 11- and l4-hydroxypodocarpatrienes which were ozonised to give the congeners (31), (34), and (36) of the naturally occurring drimanes confertifolin (6), isodrimenin (7), and winterin (8). The oxidation of a 12,13-dihydroxypodocarpatriene (37) and its dimethyl ether (38) have also been investigated. Routes for the conversion of the enone (45) and oxime (230), derived from the ozonolysis products of methyl podocarpate (10), to drimanes have also been investigated.
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