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A concise, stereoselective synthesis of (±)-geissoschizine

✍ Scribed by M.-Lluïsa Bennasar; Juan-Miguel Jiménez; Bilal A. Sufi; Joan Bosch

Publisher
Elsevier Science
Year
1996
Tongue
French
Weight
126 KB
Volume
37
Category
Article
ISSN
0040-4039

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✦ Synopsis

A stereocontrolled synthesis of (-+)-geissoschizine, involving the addition of the enolate derived from l-acetylindole to pyridinium salt 2, cyclization of the resultant 1,4-dihydropyridine, stereoselective elaboration of the E-ethylidene substituent, closure of C ring by Pummerer reaction, and methanolysis of the resulting pentacyclic lactam, is reported.

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