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