Protecting-Group-Free Total Synthesis of Anticancer (±)-Melotenine A

Adisak Thanetchaiyakup; Hassayaporn Rattanarat; Sudaporn Aree; Tanwawan Duangthongyou; Tanin Nanok; Nutthawat Chuanopparat; Paiboon Ngernmeesri

doi:10.1055/a-1633-8333

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(07): 1850-1856
DOI: 10.1055/a-1633-8333

paper

Protecting-Group-Free Total Synthesis of Anticancer (±)-Melotenine A

Autor*innen

Adisak Thanetchaiyakup

^aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand

^bCenter of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
Hassayaporn Rattanarat

^aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand

^bCenter of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
Sudaporn Aree

^aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand

^bCenter of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
Tanwawan Duangthongyou

^aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand

^bCenter of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
Tanin Nanok

^aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
Nutthawat Chuanopparat

^aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand

^bCenter of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
Paiboon Ngernmeesri ∗

^aDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand

^bCenter of Excellence for Innovation in Chemistry, Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand

Abstract

Alle Artikel dieser Rubrik

Abstract

Melotenine A, isolated from Melodinus tenuicaudatus, possesses significant anticancer activity against several human cancer cell lines. The synthesis of (±)-melotenine A was achieved without the use of any protecting groups in 11 steps with an overall yield of 6.7%. The key steps of our strategy were a Diels–Alder reaction to construct the tetracyclic framework and ring-closing metathesis to form the seven-membered ring of (±)-melotenine A.

Key words

natural product synthesis - melotenine A - anticancer agent - Diels–Alder reaction - ring-closing metathesis

Volltext

Referenzen

References
1 Feng T, Li Y, Liu Y.-P, Cai X.-H, Wang Y.-Y, Luo X.-D. Org. Lett. 2010; 12: 968

2a Zhao S, Sirasani G, Vaddypally S, Zdilla MJ, Andrade RB. Angew. Chem. Int. Ed. 2013; 52: 8309
2b Zhao S, Sirasani G, Vaddypally S, Zdilla MJ, Andrade RB. Tetrahedron 2016; 72: 6107

3 Du J.-Y, An X.-T, Zhao X.-H, Ma X.-Y, Cao Y.-X, Fan C.-A. Tetrahedron 2019; 75: 1760

4a Kuehne ME, Earley WG. Tetrahedron 1983; 39: 3707
4b Kuehne ME, Bohnert JC, Bornmann WG, Kirkemo CL, Kuehne SE, Seaton PJ, Zebovitz TC. J. Org. Chem. 1985; 50: 919

5 Chen P, Cao L, Li C. J. Org. Chem. 2009; 74: 7533
6 CCDC 2094865 (2a) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures. See the Supporting Information for details.

7a Compain P. Adv. Synth. Catal. 2007; 349: 1829
7b Wilson GO, Porter KA, Weissman H, White SR, Sottos NR, Moore JS. Adv. Synth. Catal. 2009; 351: 1817

8 Fu GC, Nguyen ST, Grubbs RH. J. Am. Chem. Soc. 1993; 115: 9856
9 Ranaivondrambola T, Hatton W, Felpin F.-X, Evain M, Mathé-Allainmat M, Lebreton J. Synlett 2010; 1631
10 Liu Y.-T, Li L.-P, Xie J.-H, Zhou Q.-L. Angew. Chem. Int. Ed. 2017; 56: 12708
11 Stavber G, Zupan M, Stavber S. Tetrahedron Lett. 2006; 47: 8463
12 Aversa MC, Barattucci A, Bonaccorsi P, Giannetto P. Tetrahedron 2002; 58: 10145
13 Jurissek C, Berger F, Eisenreich F, Kathan M, Hecht S. Angew. Chem. Int. Ed. 2019; 58: 1945
14 Guevel A.-C, Hart DJ. J. Org. Chem. 1996; 61: 465
15 Blencowe PS, Barrett AG. M. Eur. J. Org. Chem. 2014; 4844
16 Sparling BA, Moslin RM, Jamison TF. Org. Lett. 2008; 10: 1291
17 Rollin P, Pougny J.-R. Tetrahedron 1986; 42: 3479
18 Saini G, Mondal A, Kapur M. Org. Lett. 2019; 21: 9071

Zusatzmaterial

Supporting Information (PDF) (opens in new window)