6533b7d0fe1ef96bd125b9eb
RESEARCH PRODUCT
Diastereoselective synthesis of substituted 2-phenyltetrahydropyrans as useful precursors of aryl C-glycosides via selenoetherification
Michelangelo GruttadauriaSerena RielaRenato NotoPaolo Lo MeoCarmela Aprilesubject
PharmacologyC glycosidesdiastereoselctive synthesis selenoetherificationArylOrganic Chemistrychemistry.chemical_elementTetrahydropyranSettore CHIM/06 - Chimica OrganicaAnalytical Chemistrychemistry.chemical_compoundchemistryaryl C-glycosidesElectrophileOrganic chemistrySeleniumdescription
The cyclization of several substituted 5-phenyl-pent-4-en-1-ols with selenium electrophiles along some mechanistic considerations is discussed. In particular, an efficient diastereoselective synthesis of a 2,3,5,6-tetrasubstitued tetrahydropyran is reported. These findings open an interesting approach: the use of chiral selenium electrophiles for cyclization of chiral substrates. The cyclized products are useful starting material for the synthesis of D- or L-aryl C-glycosides.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2004-01-01 |