Morita-Baylis-Hillman in organic synthesis: symmetric synthesis of pyrrolizidinic and indolizidinic alkaloids

Abstract

The pyrrolizidinic and indolizidinic alkaloids are present in several plants and insects. These alkaloids are normally associated to interesting biological effects, such as, glycosidase inhibitor, anti-diabete and anti-tumorals. Some of these alkaloids are very toxic and can contaminate food and grains. Due to the biological relevance and the substitution patterns diversity exhibited by these alkaloids there are in literature several different approaches to synthesize them. This research project has as aim to using an alternative synthetic methodology recently developed by us to prepare this type of alkaloids (pyrrolizidinic and indolizidinic), in its enantiomerically pure forms. This strategy is based on the utilization of Morita-Baylis-Hillman adducts obtained from chiral aminoacids. (AU)