138596-88-0

Upstream product

• 1034128-58-9 (S)-tert-butyl 2-(2-(methoxy(methyl)amino)-2-oxoethyl)pyrrolidine-1-carboxylate 
• 89980-69-8 3,4-dimethoxyphenylmagnesium bromide 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 101130-03-4 tert-butyl (S)-2-(diazoacetyl)pyrrolidine-1-carboxylate 
• 88790-37-8 (2S)-tert-Butyl 2-(2-methoxy-2-oxoethyl)pyrrolidine-2-carboxylate 
• 50766-67-1 2-(3,4-dimethoxyphenyl)-1,3-dithiane 
• 138596-87-9 (2''S)-2-(3',4'-Dimethoxyphenyl)-2-(N-t-butoxycarbonyl-2''-methylenepyrrolidine)-1,3-dithiane 

Downstream Products

• 138664-35-4 (–)-ruspolinone 
• 1514903-65-1 (3aS,9aR)-5-(3,4-dimethoxyphenyl)-1,2,3,3a,4,6,7,8,9,9a-decahydropyrrolo[1,2-a]quinoline 
• 1514903-56-0 (S)-4-(7-(3,4-dimethoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizin-6-yl)phenol 
• 26503-67-3 (S)-1,2,3,5,8,8a-hexahydro-6,7-bis(3,4-dimethoxy-phenyl)indolizine 
• 1242597-79-0 (S)-1,2,3,5,8,8a-hexahydro-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)indolizine 

Relevant academic research and scientific papers

Iminium ion-enamine cascade cyclizations: Facile access to structurally diverse azacyclic compounds and natural products

A one-pot, mild, two-component iminium ion-enamine cascade reaction to construct structurally diverse azacyclic frameworks from l-proline and l-pipecolic acid, and its application to indolizidine and quinolizidine alkaloids and azasteroids, is reported.

Enantioselective synthesis of 2-substituted pyrrolidines via domino cross metathesis/intramolecular aza-Michael addition

A highly enantioselective intramolecular aza-Michael addition with enone carbamates catalyzed by chiral Bronsted acids was developed. A domino cross metathesis/aza-Michael addition for the preparation of 2-substituted pyrrolidines or benzopyrrolidines was also explored. The reactions described here provide an efficient asymmetric protocol for enantio-enriched heterocycles, especially 2-substituted pyrrolidines.

A total synthesis of (-)-ruspolinone

A synthesis of the pyrrolidine alkaloid (-)-ruspolinone (1) from (2S)-proline in 7 steps and 26% overall yield is presented which assigns the (2S) configuration to (-)-(1). The compound obtained by this route has [α](D)-29.73° compared to a value of zero for the material isolated from the plant suggesting racemisation had occurred during isolation.