ASYMMETRIC-SYNTHESIS OF 5-HEXADECANOLIDE, PHEROMONE OF THE QUEEN OF THE ORIENTAL HORNET, VESPA-ORIENTALIS

Authors
RAINA S SINGH VK
Citation
S. Raina et Vk. Singh, ASYMMETRIC-SYNTHESIS OF 5-HEXADECANOLIDE, PHEROMONE OF THE QUEEN OF THE ORIENTAL HORNET, VESPA-ORIENTALIS, Tetrahedron, 52(12), 1996, pp. 4479-4484
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
12
Year of publication
1996
Pages
4479 - 4484
Database
ISI
SICI code
0040-4020(1996)52:12<4479:AO5POT>2.0.ZU;2-D
Abstract
An efficient asymmetric synthesis of 5-hexadecanolide from a chiral ep oxide is described. Both the enantiomeric forms of the chiral epoxide are easily available from mannitol and ascorbic acid. The key step in the synthesis is the formation of delta-lactone from delta-hydroxy ace tal using m-CPBA and BF3 . OEt(2).