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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Synthesis of Castanospermine and Epimers by Metathesis Routes

Author(s): Ileana Dragutan, Valerian Dragutan, Albert Demonceau and Hermannus C.M. Vosloo

Volume 17 , Issue 22 , 2013

Page: [2721 - 2739] Pages: 19

DOI: 10.2174/13852728113179990114

Price: $65

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.


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