Abstract
The convenient route (showing a historical background of the co-operation between the author and late Professor Aleksander Zamojski) to carbocyclic sugar mimics: derivatives of highly oxygenated bicyclo[4.3.0]nonanes and bicyclo[ 4.4.0]decanes from sugar chirons is presented. First, the paper describes the stereoselective synthesis of higher carbon sugars (up to 21 carbon atoms in the chain) starting from various simple derivatives of carbohydrates such as: sugar phosphoranes and phosphonates, sugar acetylenes, and finally sugar allyltins. The latter turned to be convenient starting materials for the preparation of highly versatile dienoaldehydes, via a controlled fragmentation with elimination of the stannyl moiety. These dienes were used for the stereoselective synthesis of highly oxygenated carbo-bicyclic derivatives.
Keywords: Carbocyclic Sugar Mimics, stereoselective synthesis, higher carbon sugars, carbohydrates, sugar acetylenes, sugar allyltins, Witting-Typing Methodology, Hetero Diels-Alder Approach
Current Organic Chemistry
Title: From Higher Carbon Sugars to Carbocyclic Sugar Mimics
Volume: 12 Issue: 12
Author(s): Slawomir Jarosz
Affiliation:
Keywords: Carbocyclic Sugar Mimics, stereoselective synthesis, higher carbon sugars, carbohydrates, sugar acetylenes, sugar allyltins, Witting-Typing Methodology, Hetero Diels-Alder Approach
Abstract: The convenient route (showing a historical background of the co-operation between the author and late Professor Aleksander Zamojski) to carbocyclic sugar mimics: derivatives of highly oxygenated bicyclo[4.3.0]nonanes and bicyclo[ 4.4.0]decanes from sugar chirons is presented. First, the paper describes the stereoselective synthesis of higher carbon sugars (up to 21 carbon atoms in the chain) starting from various simple derivatives of carbohydrates such as: sugar phosphoranes and phosphonates, sugar acetylenes, and finally sugar allyltins. The latter turned to be convenient starting materials for the preparation of highly versatile dienoaldehydes, via a controlled fragmentation with elimination of the stannyl moiety. These dienes were used for the stereoselective synthesis of highly oxygenated carbo-bicyclic derivatives.
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Cite this article as:
Jarosz Slawomir, From Higher Carbon Sugars to Carbocyclic Sugar Mimics, Current Organic Chemistry 2008; 12 (12) . https://dx.doi.org/10.2174/138527208785161187
DOI https://dx.doi.org/10.2174/138527208785161187 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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