Search results for "Microcarpalide"

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Stereoselective Total Synthesis and Absolute Configuration of the Natural Decanolides (−)-Microcarpalide and (+)-Lethaloxin. Identity of (+)-Lethalox…

2005

[reaction: see text] Convergent, stereoselective syntheses of the pharmacologically active, naturally occurring lactones (-)-microcarpalide and (+)-lethaloxin have been achieved from the commercially available, chiral reagents (R)-glycidol, (S,S)-tartaric acid, and d-ribose as the starting materials. These syntheses have further served to establish the hitherto unknown absolute configuration of (+)-lethaloxin and to show its identity with (+)-pinolidoxin.

LethaloxinChemistryStereochemistryOrganic ChemistryMolecular ConformationAbsolute configurationTotal synthesisStereoisomerismAlkenesKetonesPinolidoxinHeterocyclic Compounds 1-RingIdentity (mathematics)AlkanesStereoselectivityMicrocarpalideThe Journal of Organic Chemistry
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Stereoselective Synthesis of Microcarpalide

2002

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]

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