SYNTHESIS OF AN UNNATURAL ANACARDIC ACID ANALOGUE

ABSTRACT

The unnatural E isomer of anacardic acid 7 has been synthesized employing the following key steps: Swern oxidation of a diastereoisomeric mixture of β-hydroxyphosphine oxides 13a/b to the corresponding ketone 14 followed by stereospecific reduction to the pure threo isomer 13b which upon treatment with sodium hydride underwent trans elimination to afford the E ester 15.

ACKNOWLEDGMENTS

The authors wish to thank the Councils of the University of the Western Cape and the National Research Foundation for financial support and to the Centre for Development Cooperative Services, The Netherlands for a bursary (FET).