6533b858fe1ef96bd12b62b8

RESEARCH PRODUCT

Stereoselective Synthesis of the Cytotoxic Macrolide FD-891

Jorge Garcia‐fortanetJuan MurgaJ. Alberto MarcoMiguel Carda

subject

Molecular StructureChemistryStereochemistryOrganic ChemistryTotal synthesisAntineoplastic AgentsStereoisomerismGeneral MedicineRing (chemistry)BiochemistryAldol reactionCytotoxic T cellStereoselectivityMacrolidesPhysical and Theoretical Chemistry

description

[reaction: see text] A total synthesis of the naturally occurring, cytotoxic macrolide FD-891 is described. Three fragments were first stereoselectively constructed using mainly asymmetric aldol and allylation reactions. The complete framework was then assembled using two Julia-Kocienski olefinations to connect the three fragments and a Yamaguchi reaction to close the macrolactone ring.

https://doi.org/10.1021/ol060669w