Journal
TETRAHEDRON
Volume 56, Issue 51, Pages 9901-9907Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(00)00961-3
Keywords
muscarinic receptor; antagonist; Michael addition; enolate
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Diastereoselective synthesis of (2R)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetic acid 1, an important component of a novel muscarinic M-3 receptor antagonist 3, was achieved via Michael addition of an enolate of chiral dioxolane 4 to (-)-dicyclopentadiene 9 in 90% de as a key step. The desired Michael adduct 10, which was easily isolated by recrystallization of a mixture of diastereomers, was submitted to retrograde Diels-Alder reaction. Subsequent hydrogenation of the resultant enone 12 gave the key intermediate 5 in 91% chemical yield from 10. (C) 2000 Elsevier Science Ltd. All rights reserved.
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