R. A. Mosey, J. J. Tepe / Tetrahedron Letters 50 (2009) 295–297
297
7. Ling, T.; Macherla, V. R.; Manam, R. R.; McArthur, K. A.; Potts, B. C. M. Org. Lett.
2007, 9, 2289–2292.
8. Caubert, V.; Massé, J.; Retailleau, P.; Langlois, N. Tetrahedron Lett. 2007, 48,
381–384.
9. Caubert, V.; Langlois, N. Tetrahedron Lett. 2006, 47, 4473–4475.
10. Mulholland, N. P.; Pattenden, G.; Walters, I. A. S. Org. Biomol. Chem. 2006, 4,
2845–2846.
In conclusion, we report a short racemic synthesis of an inter-
mediate used in the synthesis of salinosporamide A starting from
a tert-alkyl amino hydroxy carboxylic ester produced via an ene-
type reaction.
11. Reddy, L. R.; Fournier, J.-F.; Reddy, B. V. S.; Corey, E. J. Org. Lett. 2005, 7, 2699–
2701.
Acknowledgments
12. Macherla, V. R.; Mitchell, S. S.; Manam, R. R.; Reed, K. A.; Chao, T. H.; Nicholson,
B.; Deyanat-Yazdi, G.; Mai, B.; Jensen, P. R.; Fenical, W. F.; Neuteboom, S. T. C.;
Lam, K. S.; Palladino, M. A.; Potts, B. C. M. J. Med. Chem. 2005, 48, 3684–3687.
13. Hogan, P. C.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 15386–15387.
14. Reddy, L. R.; Fournier, J.-F.; Reddy, B. V. S.; Corey, E. J. J. Am. Chem. Soc. 2005,
127, 8974–8976.
We gratefully acknowledge the financial support provided by
American Cancer Society (RSG CDD-106972) and Michigan State
University. Additional thanks goes to Mr. Rahman Saleem from
Michigan State University for high resolution mass spectrometry.
15. Endo, A.; Danishefsky, S. J. J. Am. Chem. Soc. 2005, 127, 8298–8299.
16. Reddy, L. R.; Saravanan, P.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 6230–6231.
17. Roccaro, A. M.; Leleu, X.; Sacco, A.; Jia, X.; Melhem, M.; Moreau, A.-S.; Ngo, H.
T.; Runnels, J.; Azab, A.; Azab, F.; Burwick, N.; Farag, M.; Treon, S. P.; Palladino,
M. A.; Hideshima, T.; Chauhan, D.; Anderson, K. C.; Ghobrial, I. M. Blood 2008,
111, 4752–4763.
18. Ruiz, S.; Krupnik, Y.; Keating, M.; Chandra, J.; Palladino, M.; McConkey, D. Mol.
Cancer Ther. 2006, 5, 1836–1843.
19. Cusack, J. C., Jr.; Liu, R.; Xia, L.; Chao, T.-H.; Pien, C.; Niu, W.; Palombella, V. J.;
Neuteboom, S. T. C.; Palladino, M. A. Clin. Cancer Res. 2006, 12, 6758–6764.
20. Williams, P. G.; Buchanan, G. O.; Feling, R. H.; Kauffman, C. A.; Jensen, P. R.;
Fenical, W. J. Org. Chem. 2005, 70, 6196–6203.
Supplementary data
Experimental procedures, IR, 1H, and 13C NMR data for all new
compounds. Supplementary data associated with this article can be
References and notes
21. Corey, E. J.; Li, W. D. Z. Chem. Pharm. Bull. 1999, 47, 1–10.
22. Groll, M.; Huber, R.; Potts, B. C. M. J. Am. Chem. Soc. 2006, 128, 5136–5141.
23. Mosey, R. A.; Fisk, J. S.; Friebe, T. L.; Tepe, J. J. Org. Lett. 2008, 10, 825–828.
24. Fisk, J. S.; Tepe, J. J. J. Am. Chem. Soc. 2007, 129, 3058–3059.
25. Fisk, J. S.; Mosey, R. A.; Tepe, J. J. Chem. Soc. Rev. 2007, 36, 1432–1440.
26. Li, B.; Berliner, M.; Buzon, R.; Chiu, C. K.-F.; Colgan, S. T.; Kaneko, T.; Keene, N.;
Kissel, W.; Le, T.; Leeman, K. R.; Marquez, B.; Morris, R.; Newell, L.;
Wunderwald, S.; Witt, M.; Weaver, J.; Zhang, Z.; Zhang, Z. J. Org. Chem. 2006,
71, 9045–9050.
1. Feling, R. H.; Buchanan, G. O.; Mincer, T. J.; Kauffman, C. A.; Jensen, P. R.;
Fenical, W. Angew. Chem., Int. Ed. 2003, 42, 355–357.
2. Villanueva Margalef, I.; Rupnicki, L.; Lam, H. W. Tetrahedron 2008, 64, 7896–
7901.
3. Eustáquio, A. S.; Moore, B. S. Angew. Chem., Int. Ed. 2008, 47, 3936–3938.
4. Takahashi, K.; Midori, M.; Kawano, K.; Ishihara, J.; Hatakeyama, S. Angew.
Chem., Int. Ed. 2008, 47, 6244–6246.
5. Shibasaki, M.; Kanai, M.; Fukuda, N. Chem. Asian J. 2007, 2, 20–38.
6. Ma, G.; Nguyen, H.; Romo, D. Org. Lett. 2007, 9, 2143–2146.