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Studies on pyrrolidinones. Synthesis and cyclization of N ‐[α‐naphthyl‐(3,4,5‐trimethoxyphenyl)‐methyl]pyroglutamic acid
Author(s) -
Legrand Anne,
Rigo Benoît,
Hénichart JeanPierre,
Norberg Bernadette,
Camus Fabrice,
Durant FranÇOis,
Couturier Daniel
Publication year - 2000
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570370202
Subject(s) - chemistry , pyrrolidinones , saponification , trimethylsilyl , pyroglutamic acid , organic chemistry , ether , hydrobromic acid , amino acid , biochemistry
Condensation of trimethoxyphenyl naphthylcarbinol trimethylsilyl ether with methyl N ‐trimethylsilyl‐pyroglutamate yields two separable esters. The Friedel‐Crafts cyclization of the acids obtained after saponification gives analogs of azapodophylloxin. Reduction and treatment of the obtained products with hydrobromic acid yields analogs of azatoxin.