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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

A Synthesis of Triptoquinones D, E, and F from Podocarpic Acid

Richard C. Cambie, Lorna H. Mitchell and Peter S. Rutledge

Australian Journal of Chemistry 51(10) 931 - 940
Published: 1998

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).

https://doi.org/10.1071/C98020

© CSIRO 1998

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