Synthesis of (+/-)-kainic acid by dearomatising cyclisation of a lithiatedN-benzyl p-anisamide

Authors
Clayden, J Tchabanenko, K
Citation
J. Clayden et K. Tchabanenko, Synthesis of (+/-)-kainic acid by dearomatising cyclisation of a lithiatedN-benzyl p-anisamide, CHEM COMMUN, (4), 2000, pp. 317-318
Citations number
45
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
4
Year of publication
2000
Pages
317 - 318
Database
ISI
SICI code
1359-7345(2000):4<317:SO(ABD>2.0.ZU;2-6
Abstract
N-Benzyl p-anisamide 6, on lithiation with (BuLi)-Li-t in the presence of H MPA, undergoes a stereoselective anionic cyclisation with loss of aromatici ty to give a bicyclic enone which may be converted in nine steps to (+/-)-k ainic acid.