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Free keywords:
DIELS-ALDER REACTION; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; LEWIS-ACID; DIENE
Chemistry; alkaloids; asymmetric catalysis; asymmetric synthesis; indoles; Mannich reactions;
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.
