Oxazine ring construction: methods and applications
to natural product synthesis

doi:10.1007/s11458-009-0037-4

Front. Chem. China

2009, Vol. 4

Issue (3) : 249-258 https://doi.org/10.1007/s11458-009-0037-4

Research articles

Oxazine ring construction: methods and applications to natural product synthesis

Xiaobo WAN , Madeleine M. JOULLIÉ ,

Chemistry Department, University of Pennsylvania, 23 S. 34th Street, Philadelphia, PA 19104, USA;

Download: PDF(338 KB)
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract Although natural products containing a 1,2-oxazine ring are rare, more examples in this family of natural products have been discovered since trichodermamides A and B were reported in 2003. In addition to their structural novelty, these natural products possess very interesting bioactivities that are strongly dependent on their structures, making them attractive targets for investigating structure-activity relationships (SAR). In this feature article, we summarized the methodologies developed in recent years for constructing the 1,2-oxazine rings. Racemic and enantioselective total syntheses of trichodermamides A and B, based on these methodologies, are reviewed in detail.

Issue Date: 05 September 2009

Cite this article:

Madeleine M. JOULLIÉ,Xiaobo WAN. Oxazine ring construction: methods and applications to natural product synthesis[J]. Front. Chem. China, 2009, 4(3): 249-258.

URL:

https://academic.hep.com.cn/fcc/EN/10.1007/s11458-009-0037-4
https://academic.hep.com.cn/fcc/EN/Y2009/V4/I3/249

	Uchida, I.; Takase, S.; Kayakiri, H.; Kiyoto, S.; Hashimoto, M.; Tada, T.; Koda, S.; Morimoto, Y., J. Am. Chem. Soc. 1987, 109, 4108 doi: 10.1021/ja00247a043
	Garo, E.; Starks, C. M.; Jensen, P. R.; Fenical, W.; Lobkovsky, E.; Clardy, J., J. Nat. Prod. 2003, 66, 423 doi: 10.1021/np0204390
	Davis, R. A.; Longden, J.; Avery, V. M.; Healy, P. C., Bioorg. Med. Chem. Lett. 2008, 18, 2836 doi: 10.1016/j.bmcl.2008.03.090
	Capon, R. J.; Ratnayake, R.; Stewart, M.; Lacey, E.; Tennant, S.; H.Gill, J., Org. Biomol. Chem. 2005, 3, 123 doi: 10.1039/b413440k
	Seephonkai, P.; Kongsaeree, P.; Prabpai, S.; Isaka, M.; Thebtaranonth, Y., Org. Lett. 2006, 8, 3073 doi: 10.1021/ol061046l
	Stipanovic, R. D.; Howell, C. R., J. Antibiot. Tokyo. 1982, 35, 1326
	Liu, R.; Gu, Q. Q.; Zhu, W. M.; Cui, C. B.; Fan, G. T., Arch. Pharm.Res. 2005, 28, 1042 doi: 10.1007/BF02977399
	Rether, J.; Serwe, A.; Anke, T.; Erkel, G., Biol. Chem. 2007, 388, 627 doi: 10.1515/BC.2007.066
	Lu, C. D.; Zakarian, A., Angew. Chem. Int. Ed. 2008, 120, 6935 doi: 10.1002/ange.200801652
	Wan, X.; Joullié, M.M., J. Am. Chem. Soc. 2008, 130, 17236 doi: 10.1021/ja807011b
	Faragher, R.; Gilchrist, T. L., J. Chem. Soc. Chem. Commun. 1976, 581 doi: 10.1039/c39760000581
	Gilchrist, T. L.; Roberts, T. G., J. Chem. Soc. Chem. Commun. 1978, 847 doi: 10.1039/c3978000847b
	Hippeli, C.; Reissig, H.U., Synthesis 1987, 77 doi: 10.1055/s-1987-27856
	Arnold, T.; Reissig, H. U., Synlett 1990, 514 doi: 10.1055/s-1990-21147
	Nakanishi, S.; Otsuji, Y.; Itoh, K.; Hayashi, N., Bull. Chem. Soc. Jpn. 1990, 63, 3595 doi: 10.1246/bcsj.63.3595
	Nakanishi, S.; Higuchi, M.; Flood, T. C., J. Chem. Soc. Chem. Commun. 1986, 30 doi: 10.1039/c39860000030
	Song, J.; Lin, Y.; Szeto, Y. S.; Chan, W. L., Heterocycles 2006, 68, 1685 doi: 10.3987/COM-06-10737
	Tishkov, A. A.; Lesiv, A. V.; Khomutova, Y. A.; Strelenko, Y. A.; Nesterov, I. D.; Antipin, M. Y.; Ioffe, S. L.; Denmark, S. E., J. Org. Chem. 2003, 68, 9477 doi: 10.1021/jo034669a
	Sukhorukov, A. Y.; Klenov, M. S.; Ivashkin, P. E.; Lesiv, A. V.; Khomutova, Y. A.; Ioffe, S. L., Synthesis 2007, 97
	Young, I. S.; Kerr, M. A., Angew. Chem. Int. Ed. 2003, 42, 3023 doi: 10.1002/anie.200351573
	Young, I. S.; Kerr, M. A., Org. Lett. 2004, 6, 139 doi: 10.1021/ol0362919
	Ganton, M. D.; Kerr, M. A., J. Org. Chem. 2004, 69, 8554 doi: 10.1021/jo048768f
	Dumez, E.; Dulcere, J. P., Chem. Commun. 1998, 479 doi: 10.1039/a707840d
	Schade, W.; Reissig, H.U., Synlett 1999, 632 doi: 10.1055/s-1999-2662
	Reissig, H.U.; Hormuth, S.; Schade, W.; Amombo, M. O.; Watanabe, T.; Pulz, R.; Hausherr, A.; Zimmer, R., J. Heterocycl. Chem. 2000, 37, 597 doi: 10.1002/jhet.5570370316
	Schmidt, E.; Reissig, H.U.; Zimmer, R., Synthesis 2006, 2074
	Ohwada, T.; Okabe, K.; Ohta, T.; Shudo, K., Tetrahedron 1990, 46, 7539 doi: 10.1016/S0040-4020(01)89066-9
	Nakamura, S.; Uchiyama, M.; Ohwada, T., J. Am. Chem. Soc. 2003, 125, 5282 doi: 10.1021/ja0343151
	Zakarian, A.; Lu, C.D., J. Am. Chem. Soc. 2006, 128, 5356 doi: 10.1021/ja0609710
	Skorcz, J. A.; Suh, J. T.; Judd, C. I., J. Med. Chem. 1966, 9, 656 doi: 10.1021/jm00323a004
	Furukawa, M.; Sugita, M.; Kojima, Y.; Hayashi, S., Chem. Pharm. Bull. 1973, 21, 2099
	Stanek, J.; Frei, J.; Mett, H.; Schneider, P.; Regenass, U., J. Med. Chem. 1992, 35, 1339 doi: 10.1021/jm00086a003
	Kurbanli, S.; Sen, N.; Guler, E.; Kocak, A., Synth. Comm. 2004, 34, 1663
	Lee, V. J.; Woodward, R. B., J. Org. Chem. 1979, 44, 2487 doi: 10.1021/jo01328a033
	Al-Qawasmeh, R. A.; Al-Tel, T. H.; Abdel-Jalil, R. J.; Voelter, W., Chem. Lett. 1999, 541 doi: 10.1246/cl.1999.541
	Dang, T. T.; Albrecht, U.; Gerwien, K.; Siebert, M.; Langer, P., J. Org. Chem. 2006, 71, 2293 doi: 10.1021/jo052329e
	Wan, X.; Doridot, G.; Joullie, M. M., Org. Lett. 2007, 9, 977 doi: 10.1021/ol062993x
	Donald, J. R.; Edwards, M. G.; Taylor, R. J. K., TetrahedronLett. 2007, 48, 5201 doi: 10.1016/j.tetlet.2007.05.145
	Salmond, W. G.; Barta, M. A.; Havens, J. L., J. Org. Chem. 1978, 43, 2057 doi: 10.1021/jo00404a049
	Burlison, J. A.; Blagg, B. S. J., Org. Lett. 2006, 8, 4855 doi: 10.1021/ol061918j

Viewed

Full text

Abstract

Cited

Shared

Discussed