Amphidinolide E is a 19-membered macrolide possessing potent cytoxic activity. The macrolide core having
two key intermediates alcohol and acid was synthesized efficiently. The THF ring segment was synthesized from Dglucose
as chiral precursor, whereas the cis-tetrahydrofuran ring was established by stereoselective intramolecular oxymercuration
reaction. The acid component having E-diene was established by Stille cross coupling of vinyl iodo and vinly
stannane segment. Coupling reaction of acid segment and alcohol was examined.
Keywords: Amphidinolide, Bestmann reagent, natural product, oxymercuration, stereoselectivity, stille coupling, Takai olefination, biological, intermediates, Debenzylation
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