Abstract
| - The synthesis of “naked ” ellagitannin analogues 1 and 2, having a preferred sense of twist of thediphenyl moiety, with a rhamnose and a glucose template, is reported. A clear induction in thechirality of the diphenyl moiety, mediated through a 10-membered ring via ester linkages, wasobserved. The chiral scaffold of glucose (diequatorial 2,3-hydroxyl groups) exerts a remarkablestronger 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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