Title

Eleuthesides and their analogs: V. Medium- and large-ring lactones based on levoglucosenone.

Authors

Khalilova, Yu.; Spirikhin, L.; Salikhov, Sh.; Valeev, F.

Abstract

Ozonolysis of the bridging double bond in bicyclic enol ethers obtained by the Michael reaction and subsequent intramolecular etherification afforded chiral decanolides fused to a tetrahydropyran ring. Three-step procedures were developed for the synthesis of chiral lactones with medium and large rings via oxidative cleavage with pyridinium chlorochromate of mixed bicyclic ketals which were prepared by treatment with methanolic HCl of Michael adducts derived from levoglucosenone and cyclopenta-, cyclohexa-, cyclohepta-, and cyclododecanone.

Subjects

OZONOLYSIS; CHEMICAL bonds; BICYCLIC compounds; ENOL ethers; MICHAEL reaction; TETRAHYDROPYRANYL compounds; LACTONES

Publication

Russian Journal of Organic Chemistry, 2014, Vol 50, Issue 1, p117

ISSN

1070-4280

Publication type

Academic Journal

DOI

10.1134/S1070428014010229