REGIO AND STEREOSELECTIVITY IN THE SYNTHESIS OF A 2,2,6,6-TETRASUBSTITUTED TETRAHYDROPYRAN FROM GERANYL ACETATE - SYNTHESIS OF DIHYDROPYRANS

Authors
URONES JG DIEZ D MARCOS IS BASABE P GARRIDO NM ESCARCENA R LITHGOW AM DOMINGUEZ MF SANCHEZ JM
Citation
Jg. Urones et al., REGIO AND STEREOSELECTIVITY IN THE SYNTHESIS OF A 2,2,6,6-TETRASUBSTITUTED TETRAHYDROPYRAN FROM GERANYL ACETATE - SYNTHESIS OF DIHYDROPYRANS, Synlett, (8), 1995, pp. 855-856
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
8
Year of publication
1995
Pages
855 - 856
Database
ISI
SICI code
0936-5214(1995):8<855:RASITS>2.0.ZU;2-N
Abstract
The tetrahydropyranic fraction from the cyclization of geranyl acetate with phenylselenenic acid has only two racemic diasteroisomers that w ere separated as their hydroxyderivatives 7 and 8. The establishment o f the stereochemistry for both pairs of diasteroisomers is reported as well as the transformation of 7 and 8 into a unique racemic dihydropy rane 4, a precursor of beta-pyrones. A mechanism for the regio-stereos elective cyclization is proposed.