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SYNTHÈSE DE LA 1-DÉAZA-EUPOLAURAMINE


VÉRONIQUE RYS, AXEL COUTURE, ÉRIC DENIAU, PIERRE GRANDCLAUDON*
UNIVERSITÉ DES SCIENCES ET TECHNOLOGIES DE LILLE 1, UMR 8009 'COM', LABORATOIRE DE CHIMIE ORGANIQUE PHYSIQUE, USTL- BÂTIMENT C3(2), 59655 VILLENEUVE D'ASCQ CEDEX, FRANCE. *CORRESPONDING AUTHOR: PIERRE.GRANDCLAUDON@UNIV-LILLE1.FR

Issue:

SCSCC6, Volume VIII, No. 3

Section:

Volume VIII, No. 3 (2007)

Abstract:

A concise and efficient synthesis of 1-deaza-eupolauramine 2 is disclosed. The key steps are the connection of a metalated isoindolinone equipped with the synthetic auxiliary benzotriazolyl group with an ortho-halogenobenzaldehyde, followed by interception of the transient oxanion with bulky pivaloyl chloride. Removal of the temporary auxiliary under acidic conditions followed by free radical cyclization of the resulting enelactam derivative and ultimate replacement of the pivaloyloxy group by the methoxy functionality completes the synthesis of the targeted compound.

Keywords:

isoindolinones, benzotriazole, metalation, oxidative cyclization, alkaloids, eupolauramine.

Code [ID]:

CSCC6200708V03S01A0002 [0001963]

Full paper:

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