159154-08-2

Upstream product

• 159153-94-3 (3S,4S)-4-(N-benzylamino)-3-methyl-5-phenyl-1-penten-3-ol 
• 159154-06-0 (2S,4S,5S)-3,4-Dibenzyl-5-methyl-2-nonyl-5-vinyl-oxazolidine 
• 159153-91-0 (3S,4S)-4-(N-(benzyloxycarbonyl)amino)-3-methyl-5-phenyl-1-penten-3-ol 
• 111491-96-4 (S)-3-(N-(benzyloxycarbonyl)amino)-4-phenyl-2-butanone 
• 112-31-2 caprinaldehyde 
• 159154-07-1 (2S,3R,5S)-3-acetyl-1,2-dibenzyl-5-nonylpyrrolidine 

Downstream Products

• 159247-98-0 (2R,5S)-2-benzyl-1-methyl-5-nonyl-3-oxopyrrolidine 
• 119463-16-0 (2R,3R,5S)-2-benzyl-3-hydroxy-1-methyl-5-nonylazolidine 
• 159247-97-9 (2R,3S,5S)-2-benzyl-3-hydroxyl-1-methyl-5-nonylpyrrolidine 
• 159154-09-3 (2R,3S,5S)-3-acetyl-2-benzyl-1-(ethoxycarbonyl)-5-nonylpyrrolidine 
• 159154-10-6 (2R,3S,5S)-3-acetoxy-2-benzyl-1-(ethoxycarbonyl)-5-nonylpyrrolidine 

Relevant academic research and scientific papers

Enantioselective total synthesis of either enantiomer of the antifungal antibiotic preussin (L-657,398) from (S)-phenylalanine

Enantioselective total syntheses of the antifungal agent (+)-preussin (1) and its enantiomer (-)-1 from (S)-phenylalanine are described. The central transformations are protic acid-promoted aza-Cope rearrangement - Mannich cyclization reactions (12 → 19 and 13 → 27). Retro-Mannich fragmentation-Mannich cyclization (27 → 28) is key to the formation of (-)-1. This study demonstrates, for the first time, that enantioenriched substituted pyrrolidines can be prepared using the aza-Cope-Mannich rearrangement.