Tetrahedron: Asymmetry

Synthesis of anti-Alzheimer (R)-arundic acid

B Pelotier, O Piva

Index: Pelotier, Beatrice; Holmes, Ta'id; Piva, Olivier Tetrahedron Asymmetry, 2005 , vol. 16, # 8 p. 1513 - 1520

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Citation Number: 21

Abstract

The asymmetric synthesis of the anti-Alzheimer agent (R)-arundic acid has been performed via a diastereoselective photodeconjugation reaction as the key-step. The synthetic approach involves a readily available chiral auxiliary, diacetone-d-glucose, and allows access to either enantiomer as illustrated by the synthesis of (S)-arundic acid. Both enantiomers were obtained in 88% ee using the same chiral auxiliary.