6533b85ffe1ef96bd12c199e

RESEARCH PRODUCT

A stereoselective synthesis of (+)-malyngolide via a ring-closing olefin metathesis

Miguel CardaSantiago RodriguezJ. Alberto MarcoEncarnación Castillo

subject

chemistry.chemical_classificationAllylic rearrangementKetoneChemistryStereochemistryOrganic ChemistryErythruloseRing (chemistry)MetathesisBiochemistrychemistry.chemical_compoundRing-closing metathesisDrug DiscoveryStereoselectivityEnantiomer

description

Abstract A very short and stereoselective synthesis of the non-natural enantiomer of malyngolide from l -erythrulose is described. Key features of the synthesis are the Felkin–Anh diastereoselective allylation of a polyoxygenated ketone and the allylation/metathesis/allylic oxidation protocol recently described by our group.

https://doi.org/10.1016/s0040-4039(00)00884-4