1508319-01-4

Upstream product

• 1508318-87-3 C₁₇H₂₁NO 
• 1508318-90-8 C₂₉H₃₄N₂O₄ 
• 1508318-98-6 (R)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-3-cyclopentyl-1-(2,6-diethylpyridin-4-yl)-5-oxopent-1-yn-3-yl acetate 
• 104-15-4 toluene-4-sulfonic acid 
• 4524-93-0 Cyclopentanecarboxylic acid chloride 
• 1508318-85-1 (S)-4-benzyl-3-((R)-3-cyclopentyl-3-hydroxy-4-pentynoyl)oxazolidin-2-one 
• 132836-66-9 (S)-3-acetyl-4-benzyloxazolidin-2-one 
• 70639-95-1 cyclopentyl ethynyl ketone 
• 167303-65-3 N-Cyclopentanecarbonyl-N,O-dimethylhydroxylamine 
• 70639-94-0 3-cyclopentyl-1-trimethylsilyl-1-propyn-3-one 

Relevant academic research and scientific papers

Synthesis of filibuvir. Part I. Diastereoselective preparation of a β-hydroxy alkynyl oxazolidinone and conversion to a 6,6- disubstituted 2H-pyranone

This is the first in a series of three papers describing the identification and development of a commercial synthesis of filibuvir (1). This contribution describes development of an Evans aldol reaction to control the tertiary alcohol stereocenter, a challenging variant of that strategy in that both reacting partners were nonstandard (acetate enolate and ketone electrophile). A sequence consisting of Sonogashira coupling, acylation and hydrogenation delivered acetate 24, and Dieckmann cyclization provided β-keto lactone 2.