760947-75-9Relevant academic research and scientific papers
A practical total synthesis of (±)-cermizine D and a formal synthesis of (±)-cermizine C
Shi, Xin,Bao, Ying,Deng, Zhen-Tao,Zhu, Yu,Shao, Li-Dong,Zhang, Hong-Bin,Zhao, Qin-Shi
, p. 274 - 279 (2018)
A practical total synthesis of (±)-cermizine D and a formal synthesis of (±)-cermizine C were achieved. The four-step total synthesis comprised mainly a Michael addition, a Weinreb amide-activated substitution and a sequence of ketalation/PtO2-catalysed dearomatisation/reductive amination reactions that resulted in ring closure in 13.7% overall yield. The formal synthesis was accomplished in 29.7% overall yield.
Enantioselective approach to quinolizidines: Total synthesis of cermizine D and formal syntheses of senepodine G and cermizine C
Veerasamy, Nagarathanam,Carlson, Erik C.,Collett, Nathan D.,Saha, Mrinmoy,Carter, Rich G.
, p. 4779 - 4800 (2013/06/27)
The formal syntheses of C5-epi-senepodine G and C 5-epi-cermizine C have been accomplished through a novel diastereoselective, intramolecular amide Michael addition process. The total synthesis of cermizine D has been achieved throug
Straightforward access to enantioenriched 2-allylpiperidine: Application to the synthesis of alkaloids
Bosque, Irene,González-Gómez, José C.,Foubelo, Francisco,Yus, Miguel
, p. 780 - 784 (2012/03/26)
An efficient stereocontrolled preparation of (2R,RS)-2-allyl-(N- tert-butylsulfinyl)piperidine and its enantiomer is detailed. The sequence requires only two synthetic operations with one-column chromatography and is readily scaled up. The versatility of these chiral building blocks was exemplified by the total or formal synthesis of some natural and unnatural alkaloids.
Conjugate addition of lithiated methyl pyridines to enones
Taber, Douglass F.,Guo, Pengfei,Pirnot, Michael T.
supporting information; experimental part, p. 5737 - 5739 (2010/11/04)
Preparatively useful conjugate addition of lithiated methyl pyridines to cyclic and acyclic enones is reported. Addition of 2-picoline to 3-penten-2-one led to a concise synthesis of the alkaloids (±)-senepodine G and (±)-cermizine C.
A divergent approach for the total syntheses of cernuane-type and quinolizidine-type Lycopodium alkaloids
Nishikawa, Yasuhiro,Kitajima, Mariko,Kogure, Noriyuki,Takayama, Hiromitsu
experimental part, p. 1608 - 1617 (2009/05/09)
The divergent total syntheses of cernuane-type and quinolizidine-type Lycopodium alkaloids are described. A common intermediate 5 for the two types of alkaloids was assembled practically from (+)-citronellal via organocatalytic α-amination, followed by th
A two-step, formal [4 + 2] approach toward piperidin-4-ones via au catalysis
Cui, Li,Peng, Yu,Zhang, Liming
supporting information; experimental part, p. 8394 - 8395 (2009/10/23)
(Chemical Equation Presented) An efficient, formal [4 + 2] synthesis of synthetically valuable piperidin-4-ones from secondary amines in two steps has been achieved via a key gold catalysis without the purification of tertiary amine intermediates. This reaction is selective toward the less-substituted alkyl group and shows moderate to excellent diastereoselectivities. Its synthetic potential in alkaloid synthesis is demonstratedin a highly diastereoselective synthesis of (±)-cermizine C.
Total synthesis of (-)-senepodine G and (-)-cermizine C
Snider, Barry B.,Grabowski, James F.
, p. 1039 - 1042 (2008/02/04)
(Chemical Equation Presented) An efficient, stereospecific synthesis of the alkaloids senepodine G (2) and cermizine C (1) has been completed using the BF3·Et2O-promoted stereospecific addition of Me2CuLi to α,β-unsaturated lactam 6 to provide lactam 3, the addition of MeMgBr followed by HCl to convert 3 to senepodine G (2) (six steps, 40% overall yield), and the stereospecific NaBH4 reduction of 2 to give cermizine C (1) (seven steps, 40% overall yield).
