220502-07-8

Upstream product

• 220502-03-4 (4S,5R,7S)-7-Benzyl-5-ethyl-4-methoxy-5-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-oxepan-2-one 
• 220502-02-3 (2S,4R,5S)-2-Benzyl-4-ethyl-5-methoxy-4-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-cyclohexanone 
• 220502-01-2 (R)-2-Benzyl-4-ethyl-5-methoxy-4-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-cyclohexa-2,5-dienone 
• 220502-05-6 (S)-N-Allyl-3-((3R,5S)-5-benzyl-3-ethyl-2-oxo-tetrahydro-furan-3-yl)-3-methoxy-propionamide 
• 220502-04-5 (S)-3-((3R,5S)-5-Benzyl-3-ethyl-2-oxo-tetrahydro-furan-3-yl)-3-methoxy-propionic acid 
• 220502-06-7 (3S,4R)-4-Ethyl-4-formyl-3-methoxy-6-oxo-7-phenyl-heptanoic acid allylamide 

Downstream Products

• 220502-08-9 ((4S,4aS,7R,7aR)-4a-Ethyl-4-methoxy-2,6-dioxo-7-phenyl-octahydro-[1]pyrindin-1-yl)-acetaldehyde 
• 220502-09-0 (6S,6aS,8aR,8bS)-6a-Ethyl-1-hydroxy-6-methoxy-8a-phenyl-octahydro-cyclopenta[hi]indolizine-4,8-dione 

Relevant academic research and scientific papers

Asymmetric synthesis of the core structure of the melodinus alkaloids

The strategy developed for an asymmetric synthesis of (+)-meloscine (1) features an early incorporation of the aromatic ring in 1 as the 5-benzyl substituent in 2. The highly diastereoselective Birch reduction-alkylation 2 → 3, the unraveling of 3 to the butyrolactone carboxylic acid 7, and the Mannich cyclization 9c → 10c are the key steps in the synthesis of the core tricyclic unit in 1.