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 | Zendy

Fernandes Rodney A. | Zendy; Ingle Arun B. | Zendy; Chaudhari Dipali A. | Zendy

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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

Author(s) -

Fernandes Rodney A.,

Ingle Arun B.,

Chaudhari Dipali A.

Publication year - 2012

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201101420

Subject(s) - orthoester , claisen rearrangement , chemistry , tartrate , alcohol , enantiomer , chirality (physics) , carroll rearrangement , enantioselective synthesis , organic chemistry , catalysis , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark

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.

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