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An enantioselective synthesis of the C3-C21 segment of the macrolide immunosuppressive agent FR252921.

ABSTRACT: An enantioselective synthesis of the C3-C21 segment of the novel immunosuppressant FR252921 is described. The C12 and C13 stereogenic centers were constructed by a non-aldol process utilizing optically active 4-phenylbutyrolactone. The C18 stereogenic center was installed using Braun's highly diastereoselective acetate aldol reaction. Other key steps involved Curtius rearrangement and Horner-Wadsworth-Emmons olefination reactions.

SUBMITTER: Ghosh AK

PROVIDER: S-EPMC5094281 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature

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An enantioselective synthesis of the C3-C21 segment of the macrolide immunosuppressive agent FR252921.

Ghosh Arun K AK Rodriguez Samuel S

Tetrahedron letters 20160518 26

An enantioselective synthesis of the C3-C21 segment of the novel immunosuppressant FR252921 is described. The C12 and C13 stereogenic centers were constructed by a non-aldol process utilizing optically active 4-phenylbutyrolactone. The C18 stereogenic center was installed using Braun's highly diastereoselective acetate aldol reaction. Other key steps involved Curtius rearrangement and Horner-Wadsworth-Emmons olefination reactions. ...[more]

PMID: 27818534

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