6533b854fe1ef96bd12ae09f

RESEARCH PRODUCT

Stereoselective synthesis of the cytotoxic 14-membered macrolide aspergillide A.

Miguel CardaJ. Alberto MarcoSantiago Díaz-oltraJuan MurgaCésar A. Angulo-pachón

subject

chemistry.chemical_classificationModels MolecularCyclic compoundMagnetic Resonance SpectroscopyLightStereochemistryPhotochemistryOrganic ChemistryStereoisomerismStereoisomerismTetrahydropyranRing (chemistry)MetathesisChemical synthesisAnti-Bacterial Agentschemistry.chemical_compoundLactoneschemistryHemiacetalMacrolidesLactone

description

A stereoselective synthesis of the cytotoxic 14-membered macrolide aspergillide A has been performed. The preparation of a cis-2,6-disubstituted tetrahydropyran ring via stereoselective reduction of an intermediate cyclic hemiacetal was one key feature of the synthesis. The macrocyclic lactone ring was created by means of a ring-closing metathesis (RCM), whereby the new C=C bond displayed exclusively the undesired Z configuration. Conversion to the required E configuration was achieved via photochemical isomerization.

yearjournalcountryeditionlanguage
2010-02-09The Journal of organic chemistry
10.1021/jo9027038https://pubmed.ncbi.nlm.nih.gov/20141226