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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.