608128-73-0Relevant academic research and scientific papers
Diastereoselective Addition of Prochiral Nucleophilic Alkenes to α-Chiral N-Sulfonyl Imines
Ando, Kaori,Fettinger, James,Gutierrez, David A.,Houk, K. N.,Shaw, Jared T.
, p. 1164 - 1168 (2022/02/14)
The Lewis-acid-promoted addition of prochiral E- and Z-allyl nucleophiles to chiral α-alkoxy N-tosyl imines is described. Alkene geometry is selectively transferred to the newly formed carbon-carbon bond, resulting in stereochemical control of C1, C2, and C3 of the resulting 2-alkoxy-3-N-tosyl-4-alkyl-5-hexene products. A computational analysis to elucidate the high selectivity is also presented. This methodology was employed in the synthesis of two naturally occurring isomers of clausenamide.
Suzuki-Miyaura coupling based enantioselective synthesis of (+)-epi- Clausenamide and the enantiomer of its 3-deoxy analogue
Zhang, Lu,Zhou, Yumei,Yu, Xiaoming
, p. 1217 - 1220 (2012/06/18)
The first enantioselective synthesis of two biologically interesting close analogues of clausenamide, namely (+)-epi-clausenamide and (-)-3-deoxy-epi- clausenamide, was reported. Key steps of the synthesis included construction of the chiral pyrrolinone intermediates from d- and l-serine derivatives, introduction of the C4-phenyl by Suzuki-Miyaura coupling and establishment of the C6 configuration by a threo-selective Grignard reaction. Optimization of the key Suzuki-Miyaura coupling reaction was described in detail. Georg Thieme Verlag Stuttgart · New York.
Preparation of 4- and 6-desphenyl analogues of (-)-clausenamide and alternative synthesis of (+)-epi-clausenamide
Xue, Jian Jun,Zhou, Yu Mei,Yu, Xiao Ming
, p. 1261 - 1264 (2012/01/06)
4- and 6-desphenyl analogues of (-)-clausenamide, 6 and 7, were prepared in optical active form from commercially available d-pyroglutamic acid and the known racemic pyrrolidinone 13, respectively. In order to confirm the absolute stereochemistry of (+)-
Highly efficient and concise synthesis of both antipodes of SB204900, clausenamide, neoclausenamide, homoclausenamide and ζ-clausenamide. Implication of biosynthetic pathways of clausena alkaloids
Yang, Luo,Wang, De-Xian,Zheng, Qi-Yu,Pan, Jie,Huang, Zhi-Tang,Wang, Mei-Xiang
experimental part, p. 2628 - 2634 (2009/10/31)
The synthesis of both antipodes of N-methyl-N-[(Z)-styryl]-3-phenyloxirane- 2-carboxamide (SB204900), clausenamide, neoclausenamide, homoclausenamide and ζ-clausenamide have been accomplished using (2S,3R)- and (2R,3S)-3-phenyloxirane-2-carboxamides as the starting materials, and SB204900 was found to be a common precursor to other N-heterocyclic clausena alkaloids. Mediated by Bronsted acids under different conditions, for example, SB204900 underwent efficient and diverse alkene-epoxide cyclization, enamide-epoxide cyclization and arene-epoxide cyclization reactions to produce the five-membered N-heterocyclic neoclausenamide, its 6-epimer, the six-membered N-heterocyclic homoclausenamide and the eight-membered N-heterocyclic ζ-clausenamide, respectively, in good to excellent yields. Regiospecific oxidation of neoclausenamide and its 6-epimer afforded neoclausenamidone. Enolization of neoclausenamidone in the presence of LiOH and the subsequent protonation under kinetic conditions at -78 °C led to the epimerization of neoclausenamidone into clausenamidone. Reduction of clausenamidone using NaBH4 furnished clausenamide in high yield. The Royal Society of Chemistry 2009.
Synthesis and activity in enhancing long-term potentiation (LTP) of clausenamide stereoisomers
Feng, Zhiqiang,Li, Xingzhou,Zheng, Guojun,Huang, Liang
scheme or table, p. 2112 - 2115 (2009/12/03)
Clausenamide, isolated from aqueous extract of dry leaves of Clausena lansium, a Chinese folk medicine, was found to have potent activity in enhancing LTP and show nootropic activity in animal tests. In order to discovery more potent stereoisomers and to
