6533b853fe1ef96bd12ad4fa

RESEARCH PRODUCT

Syntheses of (+)-alismoxide and (+)-4-epi-alismoxide.

Gonzalo BlayB. GarciaEva MolinaJosé R. Pedro

subject

GuaninebiologyMolecular StructureChemistryStereochemistryOrganic ChemistryAbsolute configurationTotal synthesisRegioselectivityWaterStereoisomerismStereoisomerismAsteraceaebiology.organism_classificationChemical synthesisAzulenesSesquiterpenes GuaianeSilphium perfoliatumStereoselectivityChemoselectivity

description

The first total syntheses of (+)-alismoxide and (+)-4-epi-alismoxide are reported. Formal chemo-, regio-, and stereoselective addition of water to 10alpha-acetoxy-1alphaH,5betaH-guaia-3,6-diene afforded the target compounds after reduction. The absolute stereochemistry of (+)-alismoxide has been established. The low [alpha](D) +8.6 value indicates that significant amounts of alismoxide result from biosynthetic processes. Furthermore, the structure of the natural guaienediol isolated from Silphium perfoliatum has been corrected to (-)-alismoxide.

yearjournalcountryeditionlanguage
2006-09-26The Journal of organic chemistry
10.1021/jo061278yhttps://pubmed.ncbi.nlm.nih.gov/16995700