Bafilomycin A1 is a prominent member of the plecomacrolide family of natural products, which possess interesting biological activity.  Our synthetic efforts towards the convergent synthesis of the bafilomycin A1 polypropionate chain encompasses a three-step, reiterative methodology that consists of epoxide ring opening with an alkynyl organoalane reagent, reduction of the alkyne to form a homoallylic alcohol, and their stereoselective epoxidation to produce stereodefined 3,4-epoxy alcohols. These epoxides were used for the construction of configurationally defined stereotriads and stereotetrads in six to eight steps. These precursors were then coupled using dithiane chemistry to produced the C14�C25 polypropionate fragment of bafilomycin A1. This work was supported by NIH RISE (1R25-GM-61151-01A1) and NIH SCORE (2S06GM-08102-29)

Epoxide approach for the synthesis of the C14-C25 polypropionate fragment of bafilomycin A<sub>1</sub>

243rd National Meeting (2012)

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Epoxide approach for the synthesis of the C14-C25 polypropionate fragment of bafilomycin A1

Epoxide approach for the synthesis of the C14-C25 polypropionate fragment of bafilomycin A₁