Abstract
This article provides a fairly comprehensive overview on olefin metathesis reactions applied as pivotal steps in the total syntheses of indolizidine alkaloids belonging to the families of castanospermine, deoxycastanospermine and diastereomers thereof, natural or non-natural compounds that play multiple roles in biological processes. A well-balanced mixture of topics is proposed, covering most relevant traits of their biological activity, therapeutic applications, and structural similarities to, or differences from, other established iminosugar drugs. While mainly focussing on a critical discussion of the metathesis-based processes (RCM, CM, RRM), their promoters and conditions, their advantages and limitations, also shown is how metathesis has contributed to more efficient and shorter protocols for accessing this important class of antiviral, antitumor, antimetastatic, anti-inflammatory and immunoregulating agents.
Keywords: Olefin metathesis, Ruthenium catalysts, Iminosugars, Indolizidine alkaloids, Castanospermine, Deoxycastanospermine, Diastereomers, Biological activity.
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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