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Application of isatoic anhydride chemistry to the synthesis of racemic paraensine
Author(s) -
Coppola Gary M.,
Schuster Herbert F.
Publication year - 1984
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.5570210536
Subject(s) - chemistry , yield (engineering) , lithium (medication) , organic chemistry , sequence (biology) , ring (chemistry) , medicine , biochemistry , materials science , metallurgy , endocrinology
The alkaloid paraensine was obtained in racemic form in 84% overall yield by a two step reaction sequence which involves a hetero ring opening of N ‐methylisatoic anhydride with the lithium enolate of 4,5‐di‐hydro‐4,5,5‐trimethyl‐2(3 H )‐furanone followed by a thermal cyclization.