A Novel Asymmetric Synthesis of (+)-Deoxytylophorinine

Haining Lv; Song Xu; Shuanggang Ma; Yunbao Liu; Yong Li; Jing Qu; Shishan Yu

doi:10.1055/s-0034-1380137

Synthesis, Table of Contents

Synthesis 2015; 47(10): 1399-1404
DOI: 10.1055/s-0034-1380137

paper

A Novel Asymmetric Synthesis of (+)-Deoxytylophorinine

Authors

Haining Lv

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China Email: yushishan@imm.ac.cn
Song Xu

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China Email: yushishan@imm.ac.cn
Shuanggang Ma

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China Email: yushishan@imm.ac.cn
Yunbao Liu

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China Email: yushishan@imm.ac.cn
Yong Li

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China Email: yushishan@imm.ac.cn
Jing Qu

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China Email: yushishan@imm.ac.cn
Shishan Yu*

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China Email: yushishan@imm.ac.cn

Abstract

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Abstract

A novel asymmetric synthesis of a phenanthroindolizidine alkaloid, (+)-deoxytylophorinine, is reported, which uses a chiral nickel(II) complex of a glycine Schiff base to synthesize a substituted (R)-3-phenanthrylalanine as a key intermediate and Meldrum’s acid to construct the E ring.

Key words

phenanthroindolizidine alkaloids - (+)-deoxytylophorinine - asymmetric synthesis - anticancer agents - non-proteinogenic α-amino acids

Full Text

References

References
1 Govindachari TR, Viswanathan N. Heterocycles 1978; 11: 587
2 Mulchandani NB, Venkatachalam SR. Phytochemistry 1984; 23: 1206
3 Huang XS, Gao S, Fan LH, Yu SS, Liang XT. Planta Med. 2004; 70: 441
4 Komatsu H, Watanabe M, Ohyama M, Enya T, Koyama K. J. Med. Chem. 2001; 44: 1833
5 Yang CW, Chuang TH, Wu PL, Huang WH, Lee SJ. Biochem. Biophys. Res. Commun. 2007; 354: 942
6 Baumgartner B, Erdelmeier CA. J, Wright AD, Rali T, Sticher O. Phytochemistry 1990; 29: 3327
7 Liu ZJ, Lv HN, Li HY, Zhang Y, Zhang HJ, Su FQ, Xu S, Li Y, Si YK, Yu SS, Chen XG. Chemotherapy 2011; 57: 310
8 Liu ZJ, Lv HN, Li HY, Zhang Y, Zhang HJ, Su FQ, Si YK, Yu SS, Chen XG. J. Asian Nat. Prod. Res. 2011; 13: 400
9 Lv HN, Ren JH, Ma SG, Xu S, Qu J, Liu ZJ, Zhou Q, Chen XG, Yu SS. PLoS ONE 2012; 7: e30342
10 Wolfe JP, Mai DN. J. Am. Chem. Soc. 2010; 132: 12157
11 Kim S, Lee T, Lee E, Lee J, Fan G, Lee SK, Kim D. J. Org. Chem. 2004; 69: 3144
12 Marchini P, Belleau B. Can. J. Chem. 1958; 36: 581
13 Buckley TF, Rapoport H. J. Org. Chem. 1983; 48: 4222
14 Yang XM, Shi Q, Bastow KF, Lee KH. Org. Lett. 2010; 12: 1416
15 Lebrun S, Couture A, Deniau E, Grandolaudon P. Tetrahedron 1999; 55: 2659
16 Han GF, Liu YX, Wang QM. Org. Lett. 2013; 15: 5334
17 Wang ZW, Li Z, Wang KL, Wang QM. Eur. J. Org. Chem. 2010; 292

18a Belokon’ YN. Pure Appl. Chem. 1992; 64: 1917
18b Soloshonok VA, Avilov DV, Kukhar VP, Tararov VI, Savel’eva TF, Churkina TD, Ikonnikov NS, Kochetkov KA, Orlova SA, Pysarevsky AP, Struchkov YT, Raevsky NI, Belokon’ YN. Tetrahedron: Asymmetry 1995; 6: 1741

19 Belokon’ YN, Tararov VI, Maleev VI, Savel’eva TF, Ryzhov MG. Tetrahedron: Asymmetry 1998; 9: 4249
20 Saghyan AS, Dadayan AS, Dadayan SA, Mkrtchyan AF, Geolchanyan AV, Manasyan LL, Ajvazyan HR, Khrustalev VN, Hambardzumyan HH, Maleev VI. Tetrahedron: Asymmetry 2010; 21: 2956
21 Yang XM, Shi Q, Lai CY, Chen CY, Ohkoshi E, Yang SC, Wang CY, Bastow KF, Wu TS, Pan SL, Teng CM, Yang PC, Lee KH. J. Med. Chem. 2012; 55: 6751
22 Wang X, Monte WT, Napier JJ, Ghannam AN. Tetrahedron Lett. 1994; 35: 9323
23 Smreina M, Majer P, Majerová E, Guerassina TA, Eissenatat MA. Tetrahedron 1997; 53: 12867

Supplementary Material

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