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Induction of a preferred sense of twist in flexible diphenyls by carbohydrate scaffolds. Synthesis of two "naked" ellagitannin analogous.

Authors
  • Capozzi, G
  • Ciampi, C
  • Delogu, G
  • Menichetti, S
  • Nativi, C
Type
Published Article
Journal
The Journal of organic chemistry
Publication Date
Dec 28, 2001
Volume
66
Issue
26
Pages
8787–8792
Identifiers
PMID: 11749607
Source
Medline
License
Unknown

Abstract

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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