67257-68-5Relevant academic research and scientific papers
Biomimetic Approach toward the Total Synthesis of rac-2-(Acylmethylene)pyrrolidine Alkaloids
Shih, Yu-Chiao,Tsai, Pei-Hua,Hsu, Chia-Chun,Chang, Chih-Wei,Jhong, Yuandong,Chen, Yun-Chung,Chien, Tun-Cheng
, p. 6669 - 6678 (2015/10/06)
2-(Acylmethylene)pyrrolidine derivatives were synthesized via intermolecular decarbonylative Mannich reaction from various methyl ketones and 1-alkyl-1-pyrroliniums, generated in situ from 1-alkylprolines. This approach mimics the biosynthetic pathway and provides a direct access to a series of 2-(acylmethylene)pyrrolidine alkaloids, including hygrine, N-methylruspolinone, dehydrodarlinine, and ruspolinone.
Alkaloids of Cryptocarya phyllostemon
Cave, Andre,Leboeuf, Michel,Moskowitz, Henri,Ranaivo, Anissa,Bick, I. Ralph C.,et al.
, p. 2243 - 2263 (2007/10/02)
The known alkaloids (-)-antofine (1), dehydroantofine (5), (-)-cryptowoline (6), (-)-cryptowolidine (7), and (-)-cryptowolinol (8), were isolated from the New Caledonian lauraceous plant Cryptocarya phyllostemon, together with five new bases : two secophenanthroindolizidines, (-)-phyllostemine (2) and (-)-phyllosteminine (3), one pyrrolidinylacetophenone, (-)-phyllostone (4), and two quaternary tetrahydrobenzylisoquinolines, (+)-phyllocryptine (9) and (+)-phyllocryptonine (10).Chemical and spectroscopic methods were used for identification and structural investigation.A synthesis of phyllocryptonine has permitted its stereostructure to be determined.
THE APPLICATION OF THE SULPHIDE CONTRACTION TO THE SYNTHESIS OF SOME SIMPLE PYRROLIDINE ALKALOIDS
Ghirlando, Rodolfo,Howard, Arthur S.,Katz, Ruth B.,Michael, Joseph P.
, p. 2879 - 2884 (2007/10/02)
The alkaloids (+/-)-hygrine, (+/-)-dehydrodarlinine, (+/-)-dehydrodarlingianine, and (+/-)-N-methylruspolinone have been synthesised by selective reduction of vinylogous amides formed by sulphide contraction of the salts prepared by reaction of N-methyl-2
NOVEL APPLICATIONS OF THE MODIFIED POLONOVSKII REACTION - IV. PREPARATION OF (+/-)-HYGRINE AND (+/-)-N-METHYLRUSPOLINONE
Langenskioeld, Tord,Lounasmaa, Mauri
, p. 671 - 675 (2007/10/02)
Preparation of (+/-)-hygrine 5 and (+/-)-N-methylruspolinone 6 via N-methyl-2-cyanopyrrolidine 1 is described.
