6533b7d1fe1ef96bd125c3a4

RESEARCH PRODUCT

Stereoselective Synthesis of Microcarpalide

Miguel CardaJuan MurgaJ. Alberto MarcoJorge Garcia‐fortanetEva Falomir

subject

Molecular StructureChemistryStereochemistryOrganic ChemistryFungiTotal synthesisStereoisomerismAlcoholGeneral MedicineMetathesisBiochemistryTurn (biochemistry)Heterocyclic Compounds 1-Ringchemistry.chemical_compoundAlkanesStereoselectivityPhysical and Theoretical ChemistryMicrocarpalide

description

The first total synthesis of the naturally occurring nonenolide, microcarpalide, is described. The key step in the synthesis was the ring-closing metathesis of a dienic ester prepared in turn by coupling an acid and an alcohol stereoselectively synthesized from (S,S)-tartaric acid and (R)-glycidol, respectively. [structure: see text]

https://doi.org/10.1021/ol0265463