482-22-4Relevant articles and documents
Total Synthesis of Cryptopleurine and Its Analogues
Takasu, Kiyosei,Tateishi, Kaito,Yamakawa, Takuro,Yamaoka, Yousuke
, (2022/03/08)
Total synthesis of phenanthroquinolizidine alkaloid cryptopleurine was achieved in 8 steps from commercially available 2-pyridinecarboxaldehyde and the epoxide derived from methyleugenol. The key intermediate vinyl triflate enables the divergent synthesis of cryptopleurine derivatives by late-stage installation of various substituents on the C-ring.
Synthesis and biological evaluation of (-)-6-O-desmethylcryptopleurine and analogs
Liéby-Muller, Frédéric,Marion, Frédéric,Schmitt, Philippe,Annereau, Jean-Philippe,Kruczynski, Anna,Guilbaud, Nicolas,Bailly, Christian
, p. 184 - 187 (2015/04/13)
(-)-Cryptopleurine 1 is one of the most potent anti-proliferative member of the phenanthroquinolizidine class of alkaloids. We report here the synthesis of (-)-6-O-desmethylcryptopleurine (-)-2 and (-)-6-O-desmethyl-(15R)-hydroxycryptopleurine (-)-4 in th
Collective asymmetric synthesis of (-)-Antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine with tert- butanesulfinamide as a chiral auxiliary
Zheng, Yanlong,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 3348 - 3357 (2014/05/06)
A collective asymmetric synthesis of phenanthroindolizidine and phenanthroquinolizidine alkaloids (-)-antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine was achieved by means of a reaction sequence involving efficient generation of chiral homoallylic amine intermediates by asymmetric allylation of the corresponding tert-butanesulfinyl imine. From these intermediates, the pyrrolidine and piperidine rings were constructed by means of an intramolecular SN2 substitution reaction and a ring-closing metathesis reaction, respectively. The unusual C5-methoxy-substituted phenanthrene moiety of (-)-tylocrebrine was generated by means of an InCl3-catalyzed cycloisomerization reaction of an o-propargylbiaryl compound.