328583-84-2

Upstream product

• 105500-35-4 (1R,2S,6R,7S)-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one 
• 116907-30-3 (2R,5R)-2-(tert-butyl)-5-phenyl-1,3-dioxolan-4-one 

Downstream Products

• 203321-54-4 (2R,5R)-2-(t-butyl)-5-[(1S)-3-oxocyclopentyl]-5-phenyl-1,3-dioxolan-4-one 
• 328583-87-5 (2R,5R)-2-tert-butyl-5-[(1R)-4-oxo-2-cyclopentenyl]-5-phenyl-1,3-dioxolan-4-one 

Relevant academic research and scientific papers

Diastereoselective synthesis of the acid part of a new muscarinic M3 receptor antagonist

Diastereoselective synthesis of (2R)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetic acid 1, an important component of a novel muscarinic M3 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.