RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2014; 25(2): 157-162
DOI: 10.1055/s-0033-1340160
DOI: 10.1055/s-0033-1340160
synpacts
Synthesis of Tryptophan-Based Dimeric Diketopiperazine Alkaloids Using Bioinspired Reactions
Weitere Informationen
Publikationsverlauf
Received: 12. August 2013
Accepted after revision: 27. September 2013
Publikationsdatum:
05. November 2013 (online)
Abstract
Tryptophan-based dimeric diketopiperazine alkaloids such as ditryptophenaline, WIN 64821, naseseazine A, and naseseazine B, exhibit a unique architecture and interesting biological activity. These alkaloids have been the subject of intense study by the synthetic organic chemistry community, and several elegant total syntheses have been discovered, especially using bioinspired strategies. Described herein is a brief overview of these alkaloid syntheses via bioinspired transformations as key steps.
-
References
- 1 Cordell GA, Saxton JE In The Alkaloids: Chemistry and Physiology . Vol. 20. Academic Press; New York: 1981: 3-295
- 2 Hino T, Nakagawa M In The Alkaloids: Chemistry and Pharmacology . Vol. 34. Brossi A. Chap. 1 Academic Press; New York: 1989: 1-75
- 3 Anthoni U, Christophersen C, Nielsen PH. Chemistry and Reactions of Cyclic Tautomers of Tryptamines and Tryptophans . In Alkaloids: Chemical and Biological Perspectives . Vol. 13. Pelletier SW. Chap. 2 Pergamon Press; London: 1999: 163-236
- 4 Springer JP, Büchi G, Kobbe B, Demain AL, Clardy J. Tetrahedron Lett. 1977; 18: 2403
- 5 Nakagawa M, Sugumi H, Kodato S, Hino T. Tetrahedron Lett. 1981; 22: 5323
- 6 Maes CM, Potgieter M, Steven PS. J. Chem. Soc., Perkin Trans. 1 1986; 861
- 7 Barrow CJ, Cai P, Snyder JK, Sedlock DM, Sun HH, Cooper R. J. Org. Chem. 1993; 58: 6016
- 8 Popp JL, Musza LL, Barrow CJ, Rudewicz PJ, Houck DR. J. Antibiot. 1994; 47: 411
- 9 Oleynek JJ, Sedlock DM, Barrow CJ, Appell KC, Casiano F, Haycock D, Ward SJ, Kaplita P, Gillum AM. J. Antibiot. 1994; 47: 399
- 10 Sedlock DM, Barrow CJ, Brownell JE, Hong A, Gillum AM, Houck DR. J. Antibiot. 1994; 47: 391
- 11 Hiramoto M, Shibazaki M, Miyata H, Saita Y. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1994; 36: 557
- 12 Barrow CJ, Musza LL, Cooper R. Bioorg. Med. Chem. Lett. 1995; 5: 377
- 13 Kim J, Movassaghi M. Chem. Soc. Rev. 2009; 38: 3035
- 14 Schmidt MA, Movassaghi M. Synlett 2008; 313
- 15 Steven A, Overman LE. Angew. Chem. Int. Ed. 2007; 46: 5488
- 16 Raju R, Piggott AM, Conte M, Aalbersberg WG. L, Feussner K, Capon RJ. Org. Lett. 2009; 11: 3862
- 17 Kim J, Movassaghi M. J. Am. Chem. Soc. 2011; 133: 14940
- 18 Govek SP, Overman LE. Tetrahedron 2007; 63: 8499
- 19 DeLorbe JE, Jabri SY, Mennen SM, Overman LE, Zhang F.-L. J. Am. Chem. Soc. 2011; 133: 6549
- 20 Boyer N, Movassaghi M. Chem. Sci. 2012; 3: 1798
- 21 Hall SE, McCapera F, Scott AI. Tetrahedron 1967; 23: 4131
- 22 Hino T, Kodato S, Takahashi K, Yamaguchi H, Nakagawa M. Tetrahedron Lett. 1978; 19: 4913
- 23 Ishikawa H, Takayama H, Aimi N. Tetrahedron Lett. 2002; 43: 5637
- 24 Overman LE, Paone DV. J. Am. Chem. Soc. 2001; 123: 9465
- 25 Movassaghi M, Schmidt MA, Ashenhurst JA. Angew. Chem. Int. Ed. 2008; 47: 1485
- 26 Kim J, Ashenhurst JA, Movassaghi M. Science 2009; 324: 238
- 27 Kim J, Movassaghi M. J. Am. Chem. Soc. 2010; 132: 14376
- 28 Iwasa E, Hamashima Y, Fujishiro S, Higuchi E, Ito A, Yoshida M, Sodeoka M. J. Am. Chem. Soc. 2010; 132: 4078
- 29 Iwasa E, Hamashima Y, Fujishiro S, Hashizume D, Sodeoka M. Tetrahedron 2011; 67: 6587
- 30 Sodeoka M, Dodo K, Teng Y, Iuchi K, Hamashima Y, Iwasa E, Fujishiro S. Pure Appl. Chem. 2012; 84: 1369
- 31 Movassaghi M, Ahmad OK, Lathrop SP. J. Am. Chem. Soc. 2011; 133: 13002
- 32 Pérez-Balado C, de Lera ÁR. Org. Lett. 2008; 10: 3701
- 33 Pérez-Balado C, Rodríguez-Graña P, de Lera ÁR. Chem. Eur. J. 2009; 15: 9928
- 34 Kieffer ME, Chuang KV, Reisman SE. J. Am. Chem. Soc. 2013; 135: 5557
- 35 Ishikawa H, Colby DA, Boger DL. J. Am. Chem. Soc. 2008; 130: 420
- 36 Ishikawa H, Colby DA, Seto S, Va P, Tam A, Kakei H, Rayl TJ, Hwang I, Boger DL. J. Am. Chem. Soc. 2009; 131: 4904
- 37 Gotoh H, Sears JE, Eschenmoser A, Boger DL. J. Am. Chem. Soc. 2012; 134: 13240
- 38 Tadano S, Mukaeda Y, Ishikawa H. Angew. Chem. Int. Ed. 2013; 52: 7990
- 39 Kunishima M, Kawachi C, Iwasaki F, Terao K, Tani S. Tetrahedron Lett. 1999; 40: 5327
- 40 Kunishima M, Kawachi C, Morita J, Terao K, Iwasaki F, Tani S. Tetrahedron 1999; 55: 13159
- 41 Kunishima M, Kitao A, Kawachi C, Watanabe Y, Iguchi S, Hioki K, Tani S. Chem. Pharm. Bull. 2002; 50: 549