Synthetic studies toward the mitomycins: construction of the tetracyclic core via a reductive aminocyclization reaction

Tetrahedron Letters

Volumn 50, Issue 29, 2009, Pages 4265-4267

  Gubler, Daniel A ^a   Williams, Robert M ^a,b  

^a Department of Environmental and Radiological Health Sciences   (United States)

^b UNIVERSITY OF COLORADO CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE; BENZAZOCINE DERIVATIVE; MITOMYCIN DERIVATIVE; MITOMYCIN K; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CYCLIZATION; HYDROGENATION; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION; REDUCTIVE AMINOCYCLIZATION;

EID: 66149185296     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.05.004     Document Type: Article

References (17)

1. Hata T., Sano Y., Sugawara R., Matsumae A., Kanamori K., Shima T., and Hoshi T. J. Antibiot. 9 (1956) 141-146
2. Rajski S.R., and Williams R.M. Chem. Rev. 98 (1998) 2723-2795
3. Iyer V.N., and Szybalski W.A. Proc. Natl. Acad. Sci. U.S.A. 50 (1963) 355-361
4. Rajski S.R., Rollins S.B., and Williams R.M. J. Am. Chem. Soc. 120 (1998) 2192-2193
5. Bradner W.T. Cancer Treat. Rev. 7 (2001) 35-50
6. For a review on Kishi's synthesis of mitomycins A, B, and C see:. Kishi Y. J. Nat. Prod. 42 (1979) 549-568
7. For a review of Fukuyama's synthesis of mitomycins A and C see:. Fukuyama T., and Yang L. Studi. Nat. Prod. Chem. 13 (1993) 433-471
8. For a review on Danishefsky's synthetic efforts towards the mitomycins including the total synthesis of mitomycin K see:. Danishefsky S.J., and Schkeryantz J.M. Synlett (1995) 475-490
9. Synthesis of Mitomycin K:. Wang Z., and Jimenez L.S. Tetrahedron Lett. 37 (1996) 6049-6052
10. Judd T.C., and Williams R.M. J. Org. Chem. 69 (2004) 2825-2830
11. Judd T.C., and Williams R.M. Angew. Chem., Int. Ed. 41 (2002) 4683-4685
12. For a recent report of ours towards the biosynthesis of the mitomycins see:. Namiki H., Chamberland S., Gubler D.A., and Williams R.M. Org. Lett. 9 (2007) 5341-5344
13. Ducept P., Gubler D.A., and Williams R.M. Heterocycles 67 (2006) 597-619
14. Prepared according to the literature procedure:. Kitahara Y., Nakahara S., Numata R., and Kubo A. Chem. Pharm. Bull. 33 (1985) 2122-2128
15. Prepared according to the literature procedure:. Williams R.M., Rollins S.B., and Judd T.C. Tetrahedron 56 (2000) 521-532
16. Ciufolini has developed a synthesis of a fully functionalized benzazocine as part of his strategy towards the mitomycins:. Ciufolini M.A. Il Farmaco 60 (2005) 627-641
17. + 498.21, found 498.21.