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 (+)-
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
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.
