Chirality pairing recognition, a unique reaction forming spiral alkaloids from amino acids stereoselectively in one-pot

doi:10.1007/s13659-012-0003-6

Natural Products and Bioprospecting

2012, Vol. 2

Issue (2) : 53-58 DOI: 10.1007/s13659-012-0003-6

Regular Article

Chirality pairing recognition, a unique reaction forming spiral alkaloids from amino acids stereoselectively in one-pot

Bing BAI^a,c, Da-Shan LI^a, Sheng-Zhuo HUANG^a, Jie REN^a,b, Hua-Jie ZHU^a,b

a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, College of Life Science, Hebei University, Baoding, 071002, China;
c Graduate University of Chinese Academy of Sciences, Beijing 100049, China

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Abstract A novel chirality pairing recognition was found between D- and L-amino acid derivatives. Novel spiral alkaloids formed in the recognition reaction. Possible mechanism was proposed for the stereoselective and chemoselective reactions.

Keywords chirality pairing recognition reaction spiral alkaloid amino acid derivatives

Fund:Hua-Jie Zhu thanks the financial supports from NSFC(30873141), 973 Program(2009CB522300), Hebei University and the State Key Laboratory of Phytochemistry and Plant Resources in West China.

Issue Date: 11 February 2018

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Bing BAI,Da-Shan LI,Sheng-Zhuo HUANG, et al. Chirality pairing recognition, a unique reaction forming spiral alkaloids from amino acids stereoselectively in one-pot[J]. Natural Products and Bioprospecting, 2012, 2(2): 53-58.

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http://npb.kib.ac.cn/EN/10.1007/s13659-012-0003-6 OR http://npb.kib.ac.cn/EN/Y2012/V2/I2/53

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[3]	Bai, B.; Shen, L.; Ren, J.; Zhu, H. J. Adv. Syn. & Cat. 2011, accepted. Doi:10.1002/adsc.201100592.
[4]	Bou-Hamdan, F. R.; Leighton, J. L. Angew. Chem. Int. Ed. 2009, 48, 2403-2406.
[5]	(a) Intermediate 2 reacted with 1 formed only (E)-imines since the calculated energy of formation of the (Z)-imine is 5.1 kcal/mol higher than that for the (E)-imine in CH2Cl2. Two products were isolated in ratios of 2:1 to 3:1 after subsequent reactions with trans-2 and cis-2(theoretically 4:1 at the B3LYP/6-31G(d) level), respectively. (b) Nyerges, M.; Rudas, M.; Bitter, I.; Toke, L. Tetrahedron 1997, 53, 3269-3280. (c) Gomez-Monterrey, I. M.; Campiglia, P., Bertamino, A.; Aquino, C.; Mazzoni, O.; Diurno, M. V.; Iacovino, R.; Saviano, M.; Sala, M.; Novellino, E.; Grieco, P. Eur. J. Org. Chem. 2008, 1983-1992. (d) Hili, R.; Yudin, A. K. J. Am. Chem. Soc. 2006,128, 14772-14773.

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