145307-22-8Relevant articles and documents
Gram Scale Syntheses of (-)-Incarvillateine and Its Analogs. Discovery of Potent Analgesics for Neuropathic Pain
Huang, Bin,Zhang, Fengying,Yu, Gang,Song, Yan,Wang, Xintong,Wang, Meiliang,Gong, Zehui,Su, Ruibin,Jia, Yanxing
, p. 3953 - 3963 (2016)
(-)-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
Zhang, Fengying,Jia, Yanxing
, p. 6840 - 6843 (2009)
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
Ichikawa, Masaya,Aoyagi, Sakae,Kibayashi, Chihiro
, p. 2327 - 2329 (2007/10/03)
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
Ichikawa, Masaya,Takahashi, Masaki,Aoyagi, Sakae,Kibayashi, Chihiro
, p. 16553 - 16558 (2007/10/03)
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