Studies on pyrrolidinones. Synthesis and cyclization of N-[alpha-naphthyl-(3,4,5-trimethoxyphenyl)-methyl]pyroglutamic acid

Authors
Legrand, A Rigo, B Henichart, JP Norberg, B Camus, F Durant, F Couturier, D
Citation
A. Legrand et al., Studies on pyrrolidinones. Synthesis and cyclization of N-[alpha-naphthyl-(3,4,5-trimethoxyphenyl)-methyl]pyroglutamic acid, J HETERO CH, 37(2), 2000, pp. 215-227
Citations number
32
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022152X → ACNP
Volume
37
Issue
2
Year of publication
2000
Pages
215 - 227
Database
ISI
SICI code
0022-152X(200003/04)37:2<215:SOPSAC>2.0.ZU;2-9
Abstract
Condensation of trimethoxyphenyl naphthylcarbinol trimethylsilyl ether with methyl N-trimethylsilyl-pyroglutamate yields two separable esters. The Fri edel-Crafts cyclization of the acids obtained after saponification gives an alogs of azapodophylloxin. Reduction and treatment of the obtained products with hydrobromic acid yields analogs of azatoxin.