210684-40-5

Upstream product

• 210684-35-8 (2'S)-5-benzyl-2-methoxy-1-[[2'-(methoxymethyl)pyrrolidinyl]carbonyl]benzene 
• 75-03-6 ethyl iodide 

Downstream Products

• 210684-47-2 (2R,2'S)-4-benzyl-2-ethyl-2-[[2'-(methoxymethyl)pyrrolidinyl]carbonyl]-cyclohex-3-en-1-one 
• 220502-01-2 (R)-2-Benzyl-4-ethyl-5-methoxy-4-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-cyclohexa-2,5-dienone 
• 210684-59-6 (2R,3R,4S)-4-benzyl-2-ethyl-3-iodo-1-oxocyclohexane-2,4-carbolactone 
• 210684-66-5 (5R)-5-benzyl-3-ethyl-5-[(2'-hydroxycarbonyl)ethyl]furan-2(5H)-one 
• 220502-02-3 (2S,4R,5S)-2-Benzyl-4-ethyl-5-methoxy-4-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-cyclohexanone 
• 220502-03-4 (4S,5R,7S)-7-Benzyl-5-ethyl-4-methoxy-5-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-oxepan-2-one 
• 210684-80-3 3-((S)-2-Benzyl-4-ethyl-5-oxo-2,5-dihydro-furan-2-yl)-propionaldehyde 
• 210684-84-7 (S)-5-Benzyl-3-ethyl-5-(3-iodo-propyl)-5H-furan-2-one 
• 210684-78-9 (S)-5-Benzyl-3-ethyl-5-(3-hydroxy-propyl)-5H-furan-2-one 
• 210684-82-5 (S)-5-(3-Azido-propyl)-5-benzyl-3-ethyl-5H-furan-2-one 

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.

Novel fragmentation reaction of 2-alkyl- and 2,4-dialkyl-3-iodo-1- oxocyclohexan-2,4-carbolactones

2-Alkyl- and 2,4-dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones undergo lithium hydroxide- and lithium alkoxide-induced fragmentation reactions to provide butenolides, γ-hydroxycyclohexenones, and/or γ- butyrolactones. In general, product distribution is governed by two factors: (1) the nature of nucleophiles and (2) the steric bulkiness of the substituents at C-2 and C-4 of the cyclohexanones. Lithium hydroxide-induced fragmentation provides butenolides and γ-hydroxycyclohexenones. In contrast, lithium alkoxide-promoted fragmentation results in predominantly 5-substituted γ-butyrolactones along with a small amount of butenolides in limited cases. Fragmentation products induced by lithium hydroxide are largely influenced by the steric bulkiness of the substituents at C-2 and C-4 of the cyclohexanone ring. The bulky substituents render the exclusive formation of butenolides.

Asymmetric synthesis fragmentation reactions of 2-alkyl- and 2,4- dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones. Single enantiomer preparation of Δ(α,β)-butenolides, 2-alkyl-4-hydroxy-2-cyclohexen-1-ones and butyrolactones

Fragmentation reactions of keto iodolactones 4 provide access to butenolides 5,2-alkyl-4-hydroxy-2-cyclohexen-1-ones 6, and butyrolactones 9. Δ(α,β)-Butenolides 5e and 5f were converted to heterocytes 14-16 by way of intramolecular cycloaddition reactions