6533b82ffe1ef96bd1295ca0

RESEARCH PRODUCT

Stereoselective Synthesis and Structural Correction of the Naturally Occurring Lactone Stagonolide G

Santiago Díaz-oltraJ. MurgaJ. Alberto MarcoCésar A. Angulo-pachónMiguel Carda

subject

chemistry.chemical_classificationChemical transformationMolecular StructureChemistryStereochemistryOrganic ChemistryConvergent synthesisStereoisomerismStereoisomerismMetathesisRing (chemistry)BiochemistryCatalysisStereocenterHeterocyclic Compounds 1-RingLactonesStereoselectivityPhysical and Theoretical ChemistryLactone

description

A convergent synthesis of the structure proposed for the naturally occurring lactone stagonolide G is described. All three stereocenters were created with the aid of asymmetric Brown allylations. The lactone ring was built by means of a ring-closing metathesis (RCM). The synthetic and the natural compound differed in their spectral properties. A new structure is now proposed for stagonolide G and demonstrated by means of a chemical transformation.

yearjournalcountryeditionlanguage
2010-11-26Organic Letters
https://doi.org/10.1021/ol102599e