Author:
Cambie Richard C.,Mitchell Lorna H.,Rutledge Peter S.
Abstract
The First total synthesis of enantiopure triptoquinone F (6) starting from
podocarpic acid (10) is reported, as well as formal syntheses of enantiopure
triptoquinones D (4) and E (5). An acid-promoted Fries rearrangement of a
benzannulated lactone (14) has been used as a direct, moderately high yielding
route for introduction of C11 functionality. Treatment of methyl
12-methoxypodocarpa-8,11,13-trien-19-oate (11) with t-butylhydroperoxide and a
catalytic amount of ruthenium(III) chloride gives a mixture (1 : 1) of
diastereomeric t-butylcyclohexadienones (26) and (28).
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