SPIRO GAMMA-LACTONES VIA ALUMINUM ENOLATE-SPIROEPOXIDE OPENINGS

Authors
TAYLOR SK CHMIEL NH MANN EE SILVER ME VYVYAN JR
Citation
Sk. Taylor et al., SPIRO GAMMA-LACTONES VIA ALUMINUM ENOLATE-SPIROEPOXIDE OPENINGS, Synthesis, (7), 1998, pp. 1009-1014
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
7
Year of publication
1998
Pages
1009 - 1014
Database
ISI
SICI code
0039-7881(1998):7<1009:SGVAEO>2.0.ZU;2-X
Abstract
The opening of several spiroepoxides by aluminum ester enolates is des cribed. The isolated gamma-hydroxy eaters are cyclized to the correspo nding spirolactones with high efficiency. Alternatively, the crude pro duct from epoxide opening may be directly converted to the spirolacton e without purification of the intermediate hydroxy ester. This methodo logy provides another complementary route to 1-oxaspiro[4.n]-2-one sys tems that are of structural and biological interest.