A kiyooka aldol approach for the synthesis of the C(14)-C(23) segment of the diastereomeric analog of tedanolide C

Organic Letters

Volumn 13, Issue 22, 2011, Pages 6038-6041

  Bülow, Leila ^a   Naini, Arun ^a   Fohrer, Jörg ^a   Kalesse, Markus ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; CARBON; KETONE; MACROLIDE; TEDANOLIDE C;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; CARBON; KETONES; MACROLIDES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 80955129964     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202515x     Document Type: Article

References (24)

1. Ireland, C. M.; Aalbersberg, W.; Andersen, R. J.; Ayral-Kaloustian, S.; Berlinck, R.; Bernan, V.; Carter, G.; Churchill, A. C. L.; Clardy, J.; Concepcion, G. P.; Dilip De Silva, E.; Discafani, C.; Fojo, T.; Frost, P.; Gibson, D.; Greenberger, L. M.; Greenstein, M.; Harper, M. K.; Mallon, R.; Loganzo, R.; Nunes, M.; Poruchynsky, M. S.; Zask, A. Pharm Biol. 2003, 41, 15
2. Tedanolide: Schmitz, F. J.; Gunasekera, S. P.; Yalamanchili, G.; Hossain, M. B.; van der Helm, D. J. Am. Chem. Soc. 1984, 106, 7251
3. 13-Deoxytedanolide: Fusetani, N.; Sugawara, T.; Matsunaga, S. J. Org. Chem. 1991, 56, 4971
4. Candidaspongiolide: Meragelman, T. L.; Willis, R. H.; Woldemichael, C. M.; Heaton, A.; Murphy, P. T.; Snader, K. M.; Newman, D. J.; van Soest, R.; Boyd, M. R.; Cardellina, J. H.; McKee, T. C. J. Am. Prod. 2007, 70, 1133
5. Whitson, E. L.; Pluchino, K. M.; Hall, M. D.; McMahon, J. B.; McKee, T. C. Org. Lett. 2011, 13, 3518
6. Smith, A. B.; Adams, C. M.; Barbosa, S. A. L.; Degnan, P. J. Am. Chem. Soc. 2003, 125, 350
7. Smith, A. B.; Adams, C. M.; Barbosa, S. A. L.; Degnan, P. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12042
8. Julian, L. D.; Newcom, J. S.; Roush, W. R. J. Am. Chem. Soc. 2005, 127
9. Ehrlich, G.; Hassfeld, J.; Eggert, U.; Kalesse, M. J. Am. Chem. Soc. 2006, 128, 14038
10. Ehrlich, G.; Hassfeld, J.; Eggert, U.; Kalesse, M. Chem.-Eur. J. 2008, 14, 2232
11. Dunetz, J. R.; Julian, L. D.; Newcom, J. S.; Roush, W. R. J. Am. Chem. Soc. 2008, 130, 16407
12. Tedanolide, C; Chevallier, C.; Bugni, T. S.; Feng, X.; Harper, M. K.; Orendt, A. M.; Ireland, C. M. J. Org. Chem. 2006, 71, 2510
13. Taylor, R. E. Nat. Prod. Rep. 2008, 25, 854
14. Roy, M.; Kalesse, M. Nat. Prod. Rep. 2008, 25, 862
15. Barth, R; Roush, W. R. Org. Lett. 2010, 12, 2342
16. Kiyooka, S.; Kaneko, Y.; Komura, M.; Matsuo, H.; Nakano, M. J. Org. Chem. 1991, 56, 2276
17. Hayashi, Y.; Shoji, M.; Yamaguchi, J.; Sato, K.; Yamaguchi, S.; Mukaiyama, T.; Sakai, K.; Asami, Y.; Kakeya, H.; Osada, H. J. Am. Chem. Soc. 2002, 124, 12078
18. Schäckel, R.; Hinkelmann, B.; Sasse, F.; Kalesse, M. Angew. Chem., Int. Ed. 2010, 49, 1619
19. Jiao, L.; Yuan, C.; Yu, Z. J. Am. Chem. Soc. 2008, 130, 4421
20. Ehrlich, G.; Kalesse, M. Synlett 2005, 4, 655
21. Chen, C.; Namba, K.; Kishi, Y. Org. Lett. 2009, 11, 409
22. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512
23. Hillier, M. C.; Meyers, A. T. Tetrahedron Lett. 2001, 42, 5145
24. Kiyooka, S.-I.; Shahid, K. A. Tetrahedron: Asymmetry 2000, 11, 1537