An "aprotic" Tamao oxidation/syn-selective tautomerization reaction for the efficient synthesis of the C(1)-C(9) fragment of fludelone

Organic Letters

Volumn 14, Issue 18, 2012, Pages 4890-4893

  Harrison, Tyler J ^a   Rabbat, Philippe M A ^a   Leighton, James L ^a  

^a Columbia University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; EPOTHILONE DERIVATIVE; FLUDELONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ALKENES; ALKYNES; EPOTHILONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 84868246662     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302221s     Document Type: Article

References (24)

1. (a) Altmann, K.-H.; Pfeiffer, B.; Arseniyadis, S.; Pratt, B. A.; Nicolaou, K. C. ChemMedChem 2007, 2, 396.
2. (b) Altmann, K.-H.; Höfle, G.;Müller, R.; Mulzer, J.; Prantz, K. In Progress in the Chemistry of Organic Natural Products, Vol. 90: The Epothilones: An Outstanding Family of Anti-Tumor Agents. From Soil to the Clinic; Kinghorn, A. D., Falk, H., Kobayashi, J., Eds.; Springer: Vienna, 2009; p 260.
3. For a recent review and lead references, see: Watkins, E. B.; Chittiboyina, A. G.; Avery, M. A. Eur. J. Org. Chem. 2006, 4071.
4. (a) Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Chou, T.-C.; Dong, H.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 10913.
5. (b) Rivkin, A.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2005, 44, 2838.
6. (a) Zacuto, M. J.; Leighton, J. L. J. Am. Chem. Soc. 2000, 122, 8587.
7. (b) O'Malley, S. J.; Leighton, J. L. Angew. Chem., Int. Ed. 2001, 40, 2915.
8. (c) Zacuto,M.J.; O'Malley, S. J.; Leighton, J. L. J. Am. Chem. Soc. 2002, 124, 7890.
9. (d) Wang, X.; Meng, Q.; Nation, A. J.; Leighton, J. L. J. Am. Chem. Soc. 2002, 124, 10672.
10. (e) Schmidt, D. R.; O'Malley, S. J.; Leighton, J. L. J. Am. Chem. Soc. 2003, 125, 1190.
11. (f) Zacuto, M. J.; O'Malley, S. J.; Leighton, J. L. Tetrahedron 2003, 59, 8889.
12. (g) Schmidt, D. R.; Park, P. K.; Leighton, J. L. Org. Lett. 2003, 5, 3535.
13. (h) Wang, X.; Meng, Q.; Perl, N. R.; Xu, Y.; Leighton, J. L. J. Am. Chem. Soc. 2005, 127, 12806.
14. (i) Spletstoser, J. T.; Zacuto, M. J.; Leighton, J. L. Org. Lett. 2008, 10, 5593.
15. Harrison, T. J.; Ho, S.; Leighton, J. L. J. Am. Chem. Soc. 2011, 133, 7308.
16. Gaich, T.; Baran, P. S. J. Org. Chem. 2010, 75, 4657.
17. (a) Tamao, K.; Kakui, T.; Akita, M.; Iwahara, T.; Kanatani, R.; Yoshida, J.; Kumada, M. Tetrahedron 1983, 39, 983.
18. (b) Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599.
19. Volkert, M.; Uwai, K.; Tebbe, A.; Popkirova, B.; Wagner, M.; Kuhlmann, J.; Waldmann, H. J. Am. Chem. Soc. 2003, 125, 12749.
20. Wan, S.; Gunaydin, H.; Houk, K. N.; Floreancig, P. E. J. Am. Chem. Soc. 2007, 129, 7915.
21. Zhao, H.; Engers, D. W.; Morales, C. L.; Pagenkopf, B. L. Tetrahedron 2007, 63, 8774.
22. Zhu, C.; Shen, X.; Nelson, S. G. J. Am. Chem. Soc. 2004, 126, 5352.
23. Tamao, K.; Hayashi, T.; Ito, Y. Tetrahedron Lett. 1989, 30, 6533.
24. It is interesting to note that nitriles and H2O2 can combine to form peroxyimidic acids (with PhCN, the product is Payne's reagent; see: Payne, G. B. Tetrahedron 1962, 18, 763). Because the formation of the peroxyimidic acid seems to require mildly basic conditions (pH 8), and because we have never observed any epoxidation of the terminal alkene in these reactions, we do not believe this is relevant to the present oxidation reaction, but we cannot definitively rule it out.