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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.

SUBMITTER: Valentin EM

PROVIDER: S-EPMC3321641 | biostudies-literature | 2012 Apr

REPOSITORIES: biostudies-literature

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Concise epoxide-based synthesis of the C14-C25 bafilomycin A(1) polypropionate chain.

Valentín Elizabeth M EM Mulero Marlenne M Prieto José A JA

Tetrahedron letters 20120401 17

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 ...[more]

PMID: 22500058

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