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

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

Martin Banwell1*, Malcolm McLeod1, Rajaratnam Premraj1 and Gregory Simpson2

1 Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia
2 CSIRO 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).