Synthesis of Castanospermine and Epimers by Metathesis Routes

Olefin metathesis; Ruthenium catalysts; Iminosugars; Indolizidine alkaloids; Castanospermine; Deoxycastanospermine; Diastereomers; Biological activity

Abstract :

[en] 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.

Disciplines :

Chemistry

Author, co-author :

Dragutan, Ileana

Dragutan, Valerian

Demonceau, Albert ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Vosloo, Hermannus

Language :

English

Title :

Synthesis of Castanospermine and Epimers by Metathesis Routes

Publication date :

September 2013

Journal title :

Current Organic Chemistry

ISSN :

1385-2728

Publisher :

Bentham Science Publishers Ltd, Sharjah, United Arab Emirates

Volume :

Issue :

Pages :

2719-2737

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 07 July 2014

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Bibliography

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