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Enantioselective construction of highly functionalized indoloquinolizines - Congeners to polycyclic indole alkaloids

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons98735

Waldmann,  Herbert
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

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Citation

Lock, R., & Waldmann, H. (1997). Enantioselective construction of highly functionalized indoloquinolizines - Congeners to polycyclic indole alkaloids. CHEMISTRY-A EUROPEAN JOURNAL, 3(1), 143-151. doi:10.1002/chem.19970030122.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-71ED-8
Abstract
Indolo[2,3-a]quinolizines have been prepared in enantiomerically pure form by a very short and efficient synthetic sequence consisting of a) formation of imines of tryptophan esters, b) their enantioselective reaction with substituted silyloxydienes mediated by a chiral or an achiral boron Lewis acid, and c) subsequent ring closure initiated by conversion of the generated vinylogous amides into vinylogous imidoyl chlorides. With this strategy various substituents can be incorporated directly into the 1-position of the heterocyclic framework of complex indole alkaloids by the choice of an appropriate silyloxydiene, so that subsequent derivatization of the alkaloid precursor at this position is rendered unnecessary.