Induction of a preferred sense of twist in flexible diphenyls by carbohydrate scaffolds. Synthesis of two "naked" ellagitannin analogous.
- Published Article
The Journal of organic chemistry
- Publication Date
Dec 28, 2001
The synthesis of "naked" ellagitannin analogues 1 and 2, having a preferred sense of twist of the diphenyl moiety, with a rhamnose and a glucose template, is reported. A clear induction in the chirality of the diphenyl moiety, mediated through a 10-membered ring via ester linkages, was observed. The chiral scaffold of glucose (diequatorial 2,3-hydroxyl groups) exerts a remarkable stronger atropdiastereoselective effect onto the diphenoyl group than the rhamnose ring (axial-equatorial 2,3-hydroxyl groups), according to the Schmidt-Haslam hypothesis.
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The corresponding record at NLM can be accessed at https://www.ncbi.nlm.nih.gov/pubmed/11749607