ICCAS OpenIR
Highly efficient and concise synthesis of both antipodes of SB204900, clausenamide, neoclausenamide, homoclausenamide and zeta-clausenamide. Implication of biosynthetic pathways of clausena alkaloids
Yang, Luo; Wang, De-Xian; Zheng, Qi-Yu; Pan, Jie; Huang, Zhi-Tang; Wang, Mei-Xiang
2009
Source PublicationORGANIC & BIOMOLECULAR CHEMISTRY
ISSN1477-0520
Volume7Issue:12Pages:2628-2634
AbstractThe synthesis of both antipodes of N-methyl-N-[(Z)-styryl]-3-phenyloxirane-2-carboxamide (SB204900), clausenamide, neoclausenamide, homoclausenamide and zeta-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 zeta-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 degrees C led to the epimerization of neoclausenamidone into clausenamidone. Reduction of clausenamidone using NaBH(4) furnished clausenamide in high yield.
DOI10.1039/b901965k
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000267500200022
PublisherROYAL SOC CHEMISTRY
Citation statistics
Cited Times:34[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/67174
Collection中国科学院化学研究所
Corresponding AuthorWang, Mei-Xiang
AffiliationChinese Acad Sci, Beijing Natl Lab Mol Sci, Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Yang, Luo,Wang, De-Xian,Zheng, Qi-Yu,et al. Highly efficient and concise synthesis of both antipodes of SB204900, clausenamide, neoclausenamide, homoclausenamide and zeta-clausenamide. Implication of biosynthetic pathways of clausena alkaloids[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2009,7(12):2628-2634.
APA Yang, Luo,Wang, De-Xian,Zheng, Qi-Yu,Pan, Jie,Huang, Zhi-Tang,&Wang, Mei-Xiang.(2009).Highly efficient and concise synthesis of both antipodes of SB204900, clausenamide, neoclausenamide, homoclausenamide and zeta-clausenamide. Implication of biosynthetic pathways of clausena alkaloids.ORGANIC & BIOMOLECULAR CHEMISTRY,7(12),2628-2634.
MLA Yang, Luo,et al."Highly efficient and concise synthesis of both antipodes of SB204900, clausenamide, neoclausenamide, homoclausenamide and zeta-clausenamide. Implication of biosynthetic pathways of clausena alkaloids".ORGANIC & BIOMOLECULAR CHEMISTRY 7.12(2009):2628-2634.
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