145307-22-8

Upstream product

• 82044-96-0 (R)-(-)-2-Methyl-5-<1-(chlormethyl)vinyl>cyclohex-2-enon 
• 6485-40-1 (R)-Carvone 
• 823787-92-4 tert-butyl((1R,2S,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-3-oxocyclopentyl)methyl[(4-methylphenyl)sulfonyl]carbamate 
• 823787-98-0 (4aR,6S,7S,7aR)-6-{[tert-butyl(dimethyl)silyl]oxy}-7-methyl-4-methylene-2-[(4-methylphenyl)sulfonyl]octahydro-1H-cyclopenta[c]pyridine 
• 823787-97-9 (4aR,6S,7S,7aR)-7-methyl-4-methylene-2-[(4-methylphenyl)sulfonyl]octahydro-1H-cyclopenta[c]pyridin-6-ol 
• 823787-96-8 N-(2-iodo-allyl)-4-methyl-N-(5-methyl-4-oxo-cyclopent-2-enylmethyl)-benzenesulfonamide 
• 823787-95-7 (4aR,7S,7aS)-7-methyl-4-methylene-2-[(4-methylphenyl)sulfonyl]octahydro-6H-cyclopenta[c]pyridin-6-one 
• 823788-01-8 (4aR,6S,7S,7aR)-6-{[tert-butyl(dimethyl)silyl]oxy}-2,7-dimethyl-4-methyleneoctahydro-1H-cyclopenta[c]pyridine 
• 823787-94-6 4-methyl-N-(5-methyl-4-oxo-cyclopent-2-enylmethyl)-N-prop-2-ynyl-benzenesulfonamide 
• 823788-00-7 (4aR,6S,7S,7aR)-6-{[tert-butyl(dimethyl)silyl]oxy}-7-methyl-4-methylene-octahydro-1H-cyclopenta[c]pyridine 
• 823788-02-9 (4R,4aS,6S,7S,7aR)-2,4,7-trimethyl-octahydro-1H-cyclopenta[c]pyridin-6-yl tert-butyl(dimethyl)silyl ether 
• 823787-93-5 4-methyl-N-{[(1R,5S)-5-methyl-4-oxo-2-cyclopenten-1-yl]methyl}benzenesulfonamide 
• 823787-91-3 (2S,3R,4S)-4-{[tert-butyl(dimethyl)silyl]oxy}-3-(hydroxymethyl)-2-methylcyclopentanone 
• 823788-10-9 (1S,2S,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-3-oxocyclopentanecarbaldehyde 

Downstream Products

• 823788-09-6 bis[(4R,4aS,6R,7S,7aR)-2,4,7-trimethyloctahydro-1H-cyclopenta[c]pyridin-6-yl] 2,4-bis(3-methoxy-4-{[(4-methylphenyl)sulfonyl]oxy}phenyl)cyclobutane-1,3-dicarboxylate 

Relevant academic research and scientific papers

Gram Scale Syntheses of (-)-Incarvillateine and Its Analogs. Discovery of Potent Analgesics for Neuropathic Pain

(-)-Incarvillateine (INCA) is the major antinociceptive component of Incarvillea sinensis, which has been used to treat rheumatism and relieve pain in traditional Chinese medicine. We have developed a concise and general synthetic approach for INCA, which

Total synthesis of (-)-incarvilline and (-)-incarvillateine

An enantioselective, concise total synthesis of (-)-incarvilline and (-)-incarvillateine has been achieved in longest linear 9 steps (24.3% overall yield) and in 11 steps (16.5% overall yield) from (-)-carvone, respectively. The present synthesis features a notable Favorskii rearrangement of the O-protected chlorohydrin derivative of (-)-carvone to construct four of the five contiguous stereocenters on the bicyclic piperidine moiety and DMAP-catalyzed esterification of incarvilline with α-truxillic acid anhydride to generate incarvillateine skeleton.

Total synthesis of (-)-incarvilline

An enantioselective synthesis of (-)-incarvilline is presented, employing a three-component coupling reaction and an intramolecular enone-olefin [2+2] photocycloaddition followed by a SmI2-induced cyclobutane ring-opening reaction.

Total synthesis of (-)-incarvilline, (+)-incarvine C, and (-)-incarvillateine

The first total syntheses of new monoterpene alkaloids (-)-incarvilline, (+)-incarvine C, and (-)-incarvillateine, corresponding to the natural enantiomers, have been accomplished. The strategy for the synthesis of these natural products utilized 6-epi-in