A NEW SYNTHESIS OF ALKYLATED 2H-PYRAN-2-ONES AND ITS APPLICATION TO THE DETERMINATION OF THE RELATIVE AND ABSOLUTE-CONFIGURATION OF SUPELLAPYRONE, SEX-PHEROMONE OF THE BROWNBANDED COCKROACH, SUPELLA-LONGIPALPA

Authors
SHI XW LEAL WS LIU Z SCHRADER E MEINWALD J
Citation
Xw. Shi et al., A NEW SYNTHESIS OF ALKYLATED 2H-PYRAN-2-ONES AND ITS APPLICATION TO THE DETERMINATION OF THE RELATIVE AND ABSOLUTE-CONFIGURATION OF SUPELLAPYRONE, SEX-PHEROMONE OF THE BROWNBANDED COCKROACH, SUPELLA-LONGIPALPA, Tetrahedron letters, 36(1), 1995, pp. 71-74
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
1
Year of publication
1995
Pages
71 - 74
Database
ISI
SICI code
0040-4039(1995)36:1<71:ANSOA2>2.0.ZU;2-S
Abstract
The sex pheromone of the brownbanded cockroach, Supella longipalpa, ca n be synthesized by direct coupling of a brominated pyrone with an alk ylzinc reagent. The stereochemistry of the natural pheromone has been assigned as (2'R, 5-(2',4'-dimethylheptanyl)-3-methyl-2H-pyran-2-one b y a combination of synthesis, chiral gas chromatography, and electroph ysiological measurement.