595-05-1Relevant articles and documents
Total Synthesis of (-)-Calycanthine via Iron-Catalyzed Stereoselective Oxidative Dimerization
Bai, Leiyang,Jiang, Xuefeng,Ma, Yinhao
supporting information, p. 20609 - 20615 (2021/12/17)
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.
Catalytic asymmetric total synthesis of chimonanthine, folicanthine, and calycanthine through double michael reaction of bisoxindole
Mitsunuma, Harunobu,Shibasaki, Masakatsu,Kanai, Motomu,Matsunaga, Shigeki
, p. 5217 - 5221 (2012/07/27)
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
Direct stereo- and enantiocontrolled synthesis of vicinal stereogenic quaternary carbon centers. Total syntheses of meso- and (-)-chimonanthine and (+)-calycanthine [4]
Overman, Larry E.,Paone, Daniel V.,Stearns, Brian A.
, p. 7702 - 7703 (2007/10/03)
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