Synthesis of Pyridoacridines through Anionic Cascade Ring Closure

Ida Nymann Petersen; Jesper Langgaard Kristensen

doi:10.1055/s-0033-1338609

Synthesis, Table of Contents

Synthesis 2014; 46(11): 1469-1474
DOI: 10.1055/s-0033-1338609

paper

Synthesis of Pyridoacridines through Anionic Cascade Ring Closure

Ida Nymann Petersen

Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen, Denmark Fax: +4535336040 Email: jesper.kristensen@sund.ku.dk

,

Jesper Langgaard Kristensen*

Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen, Denmark Fax: +4535336040 Email: jesper.kristensen@sund.ku.dk

› Author Affiliations

Abstract

All articles of this category

Abstract

A new synthesis of 13-deazaascididemin (AK-37) based on a recently developed anionic cascade ring closure is presented. Although the isolated yields are modest, the approach provides ready access to new substituted derivatives of 13-deazaascididemin.

Key words

fused ring systems - natural products - cross coupling - anionic cascade ring closure - oxidation

Full Text

References

References
1 Marshall KM, Barrows LR. Nat. Prod. Rep. 2004; 21: 731
2 Kobayashi J, Cheng J, Nakamura H, Ohizumi Y, Hirata Y, Sasaki T, Ohta T, Nozoe S. Tetrahedron Lett. 1988; 29: 1177

3a Molinski TF. Chem. Rev. 1993; 93: 1825
3b Delfourne E, Kiss R, Le Corre L, Merza J, Bastide J, Frydman A, Darro F. Bioorg. Med. Chem. 2003; 11: 4351
3c Delfourne E, Kiss R, Le Corre L, Dujols F, Bastide J, Collignon F, Lesur B, Frydman A, Darro F. Bioorg. Med. Chem. 2004; 12: 3987
3d Belmont P, Bosson J, Godet T, Tiano M. Anticancer Agents Med. Chem. 2007; 7: 139
3e Boiffier L, Gosse I, Demenuynck M, Mailley P. Bioelectrochemistry 2012; 88: 103

4a Bracher F. Heterocycles 1989; 29: 2093
4b Cuerva JM, Cardenas DJ, Echavarren AM. J. Chem. Soc., Perkin Trans. 1 2002; 1360
4c Cuerva JM, Cardenas DJ, Echavarren AM. Chem. Commun. 1999; 1721
4d Gellerman G, Rudi A, Kashman Y. Synthesis 1994; 239
4e Moody CJ, Rees CW, Thomas R. Tetrahedron 1992; 48: 3589
4f Alvarez M, Feliu L, Ajana W, Joule JA, Fernández-Puentes JL. Eur. J. Org. Chem. 2000; 849
4g Delfourne E, Bastide J. Med. Res. Rev. 2003; 23: 234

5 Marshall KM, Holden JA, Koller A, Kashman Y, Copp BR, Barrows LR. Anti-Cancer Drugs 2004; 15: 907

6a Peterson JR, Zjawiony JK, Liu S, Hufford CD, Clark AM, Rogers RD. J. Med. Chem. 1992; 35: 4069
6b Raeder S, Bracher F. Arch. Pharm. 2012; 345: 822
6c Koller A, Rudi A, Gravalos MG, Kashman Y. Molecules 2001; 6: 300
6d Lindsay BS, Pearce AN, Copp BR. Synth. Commun. 1997; 27: 2587

7a Petersen IN, Crestey F, Kristensen JL. Chem. Commun. 2012; 48: 9092

For a related anionic cascade ring closure, see:

7b Kristensen JL, Vedsø P, Begtrup M. J. Org. Chem. 2003; 68: 4091
7c Kristensen JL. Tetrahedron Lett. 2008; 49: 2351

8a Battino R, Rettich TR, Tominaga T. J. Phys. Chem. Ref. Data 1983; 12: 163
8b Dias AM. A, Bonifácio RP, Marrucho IM, Pádua AA. H, Gomes MF. C. Phys. Chem. Chem. Phys. 2003; 5: 543

9 Øpstad CL, Melø T.-B, Sliwka H.-R, Partali V. Tetrahedron 2009; 65: 7616

10a Hepburn SA, Jackson YA. Heterocycles 2006; 68: 975
10b Plodek A, Reader S, Bracher F. Tetrahedron 2013; 69: 9857

11 Iida T, Wada T, Tomimoto K, Mase T. Tetrahedron Lett. 2001; 42: 4841

For the isolation and structure elucidation of kuanoniamine A, see:

12a Carroll AR, Scheuer PJ. J. Org. Chem. 1990; 55: 4426

For synthetic efforts, see:

12b Kitahara Y, Nakahara S, Yonezawa T, Nagatsu M, Shibano Y, Kubo A. Heterocycles 1993; 36: 943
12c Lindsay BS, Pearce AN, Copp BR. Synth. Commun. 1997; 27: 2587
12d Kitahara Y, Nakahara S, Yonezawa T, Nagatsu M, Shibano Y, Kubo A. Tetrahedron 1997; 53: 17029

13 Shen K, Fu Y, Li J, Liu L, Guo Q. Tetrahedron 2007; 63: 1568
14 Nishi H, Numains T, Kobatake S. J. Mater. Chem. 2001; 21: 17249
15 Dondoni A, Fantin G, Fogagnolo M, Medici A, Pedrini P. J. Org. Chem. 1988; 53: 1748
16 Burchat AF, Chong JM, Nielsen N. J. Organomet. Chem. 1997; 542: 281

Supplementary Material

Supporting Information