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Control of Diastereoselectivity in Orthoester Johnson–Claisen Rearrangement of Tartrate-Based Allyl Alcohol: An Efficient Synthesis of Arundic Acid, a Potential Therapeutic Agent for Alzheimer's Disease

✍ Scribed by Rodney A. Fernandes; Arun B. Ingle; Dipali A. Chaudhari


Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
621 KB
Volume
2012
Category
Article
ISSN
1434-193X

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✦ Synopsis


Abstract

A diastereoselective orthoester Johnson–Claisen rearrangement has been employed in the synthesis of both enantiomers of arundic acid, a potential therapeutic agent against Alzheimer's disease. The effect of solvent, olefin geometry and alcohol chirality on the diastereoselectivity of the orthoester Johnson–Claisen rearrangement of a tartrate‐based allyl alcohol has been studied.