title: Concise epoxide-based synthesis of the C14-C25 bafilomycin A(1) polypropionate chain.
abstract: An efficient non-aldol convergent synthesis of the C14-C25 polyketide fragment of bafilomycin A(1) was completed in 16% overall yield and 8 steps in its longest linear sequence. This synthesis highlights the formation of the key fragments using a three-step sequence of epoxide cleavage, alkyne reduction, and epoxidation developed in our laboratory; starting from suitably protected enantiomeric epoxides of trans-2,3-epoxybutanol. This chemistry represents a quick asymmetric and diastereoselective construction of the polyketide chain of bafilomycin A(1), in which every stereogenic center was constructed using solely epoxide chemistry.
authors.affiliation: Department of Chemistry, University of Puerto Rico, Río Piedras Campus, PO Box 23346, San Juan, PR 00931-3346.
authors.forename: Elizabeth M
authors.initials: EM
authors.lastname: Valentín
authors.forename: Marlenne
authors.initials: M
authors.lastname: Mulero
authors.forename: José A
authors.initials: JA
authors.lastname: Prieto