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Stereoselective synthesis of highly oxygenated derivatives decalins and cyclohexanes from monosaccharides

Marta A. Kołaczek ,  Sławomir Jarosz 

Institute of Organic chemistry of the Polish Academy of Sciences (ICHOPAS), Kasprzaka 44/52, Warsaw 01-224, Poland

Abstract

Polyhydroxylated monocarbocyclic derivatives (such as 1 or 2) are known as structures of high biological activity. The bicyclic analogues, houever, although much less known possess also interesting activity. This types of compounds are considered as inhibitors of glycosidase and glycomimics.


Compound 5 has been prepered from the alliltin derivative 4 by a metodology developed in our laboratory [1].


Functionalization of either ring in 5 will be presented a leading example of such functionalization is converrsion of 5 into cyclohexane 6 via Baeyer-Villiger oxidation [2].


[1] Jarosz S.; Gaweł A. Eur. J. Org. Chem. 2005, 3415
[2] Jarosz S.; Nowogródzki M.; Kołaczek M. Tetrahedron: Asymmetry 2007, 2674

 

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Related papers

Presentation: Poster at VI Multidyscyplinarna Konferencja Nauki o Leku, by Marta A. Kołaczek
See On-line Journal of VI Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2008-02-28 22:00
Revised:   2009-06-07 00:48