- Total Synthesis of (-)-Calycanthine via Iron-Catalyzed Stereoselective Oxidative Dimerization
-
Dimeric cyclotryptamine alkaloids typically feature vicinal all-carbon quaternary stereocenters and four nitrogen atoms. In comparison with the actual biosynthetic tryptophan derivatives, we designed the 2N-featured monomer 7, aiming to construct vicinal all-carbon quaternary stereocenters via a one-step dimerization process to access the 4N-featured isomeric members of this family. In this work, we disclose the first synthetic route to access the skeleton of (-)-isocalycanthine, featuring an iron-catalyzed oxidative dimerization reaction in a catalytic single-step operation with an overwhelming control of the absolute and relative stereochemistry. This strategy has been successfully applied to the total synthesis of (-)-calycanthine and 16 isocalycanthine derivatives, which demonstrates a new synthetic pathway for dimeric cyclotryptamine alkaloids.
- Bai, Leiyang,Jiang, Xuefeng,Ma, Yinhao
-
supporting information
p. 20609 - 20615
(2021/12/17)
-
- Copper catalyzed sequential arylation-oxidative dimerization of o-haloanilides: synthesis of dimeric HPI alkaloids
-
In this communication, we report a copper catalyzed sequential arylation-oxidative dimerization reaction as the key step for the synthesis of hexahydropyrroloindole alkaloids (+)-chimonanthine, (+)-folicanthine and (-)-calycanthine.
- Shen, Xianfu,Zhou, Yongyun,Xi, Yongkai,Zhao, Jingfeng,Zhang, Hongbin
-
p. 14873 - 14876
(2015/10/06)
-
- Catalytic asymmetric total synthesis of chimonanthine, folicanthine, and calycanthine through double michael reaction of bisoxindole
-
Direct access: Sterically hindered vicinal quaternary carbon stereocenters were constructed by catalytic enantio- and diastereoselective double Michael reaction, providing straightforward access to dimeric hexahydropyrroloindole alkaloids. A Mn(4-fluorobenzoate)2/Schiff base complex and a Mg(OAc)2/benzoic acid system were used as catalysts. Copyright
- Mitsunuma, Harunobu,Shibasaki, Masakatsu,Kanai, Motomu,Matsunaga, Shigeki
-
p. 5217 - 5221
(2012/07/27)
-
- Concise total synthesis of (-)-calycanthine, (+)-chimonanthine, and (+)-folicanthine
-
Conjoined twins: An efficient and convergent strategy for the synthesis of the dimeric hexahydropyrroloindole alkaloids, (+)-chimonanthine, (+)-folicanthine, and (-)-calycanthine, is described. The simultaneous formation of the vicinal quaternary stereocenters by using a reductive dimerization reaction provides an access to the optically active key intermediate on a gram scale. (Chemical Equation Presented).
- Movassaghi, Mohammad,Schmidt, Michael A.
-
p. 3725 - 3728
(2008/03/11)
-