Syntheses of stereochemically restricted lactone-type analogues of jasmonic acids

Authors
Toshima, H Aramaki, H Ichihara, A
Citation
H. Toshima et al., Syntheses of stereochemically restricted lactone-type analogues of jasmonic acids, BIOS BIOT B, 64(9), 2000, pp. 1988-1992
Citations number
11
Categorie Soggetti
Agricultural Chemistry","Biochemistry & Biophysics
Journal title
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY
ISSN journal
09168451 → ACNP
Volume
64
Issue
9
Year of publication
2000
Pages
1988 - 1992
Database
ISI
SICI code
0916-8451(200009)64:9<1988:SOSRLA>2.0.ZU;2-N
Abstract
5-Oxa-7-epi-jasmonic acid and 5-oxa-jasmonic acid, which are stereochemical ly restricted lactone-type analogues of jasmonic acids, were synthesized vi a three-component coupling of 2(5H)-furanone, tert-butyl acetate and 1-brom o-2-pentyne. After acidic deprotection of the tert-butyl esters, the (Z)-ol efin was introduced by catalytic partial reduction with the Lindlar catalys t to give the desired analogues.