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Pure Appl. Chem., Vol. 72, No. 9, pp. 1631-1634, 2000.

Total synthesis of herboxidiene, a complex polyketide from
Streptomyces species A7847*

Martin Banwell,^**1 Malcolm McLeod¹, Rajaratnam Premraj¹, and Gregory Simpson²

¹Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia; ²CSIRO Molecular Science, Bag 10, Clayton South, Victoria 3169, Australia

Abstract: A formal total synthesis of the polyketide herboxidiene (1) has been achieved by Horner-Wittig coupling of the side-chain fragment 12-epi-(2) with the tetrahydropyran-2-acetic acid derivative (3) followed by desilylation of the resulting triene (19) and hydroxyl-directed mono-epoxidation of the ensuing bis-homoallylic alcohol (20).

*Lecture presented at the 13^th International Conference on Organic Synthesis (ICOS-13), Warsaw, Poland, 1-5 July 2000.
** Corresponding author

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