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
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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