A formal synthesis of (-)-cyanolide a featuring a stereoselective mukaiyama aldol reaction and oxocarbenium reduction

Journal of Organic Chemistry

Volumn 76, Issue 19, 2011, Pages 8027-8032

  Sharpe, Robert J ^a   Jennings, Michael P ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC REACTION; DIASTEREOSELECTIVE REACTIONS; EFFICIENT SYNTHESIS; FORMAL SYNTHESIS; MARINE NATURAL PRODUCTS; MUKAIYAMA ALDOL REACTION; OXOCARBENIUM; STEREO-SELECTIVE; STEREOCENTERS; SYNTHETIC STRATEGIES;

CONDENSATION REACTIONS; STEREOSELECTIVITY; SUGARS;

SYNTHESIS (CHEMICAL);

BETA C GLYCOSIDE; CYANOLIDE A; GLYCOSIDE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CHEMICAL REACTION; DRUG ISOLATION; DRUG STRUCTURE; MUKAIYAMA REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXOCARBENIUM REDUCTION; STEREOCHEMISTRY;

ALDEHYDES; CARBON; CHEMISTRY TECHNIQUES, SYNTHETIC; MACROLIDES; OXIDATION-REDUCTION; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 80054116792     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201210u     Document Type: Article

References (34)

1. Pereira, A. R.; McCue, C. F.; Gerwick, W. H J. Nat. Prod. 2010, 73, 217.
2. (a) Steinmann, P.; Keiser, J.; Bos, R.; Tanner, M.; Utzinger J. Lancet Infect. Dis. 2006, 6, 411.
3. (b) Chitsulo, L.; Engels, D.; Montresor, A.; Savioli, L. Acta Trop. 2000, 77, 41.
4. Gryseels, B.; Polman, K.; Clerinx, J.; Kestens, L. Lancet 2006, 368, 1106.
5. (a) Rao, M. R.; Faulkner, D. J. J. Nat. Prod. 2002, 65, 386.
6. (b) Erickson, K. L.; Gustafson, K. R.; Pannell, L. K.; Beutler, J. A.; Boyd, M. R. J. Nat. Prod. 2002, 65, 1303.
7. (c) Hajare, A. K.; Ravikumar, V.; Khaleel, S.; Bhuniya, D.; Reddy, D. S. J. Org. Chem. 2011, 76, 963.
8. (d) Yang, Z.; Xie, X.; Jing, P.; Zhao, G.; Zheng, J.; Zhao, C.; She, X. Org. Biomol. Chem. 2011, 9, 984.
9. (e) Pabbaraja, S.; Satyanarayana, K.; Ganganna, B.; Yadav, J. S. J. Org. Chem. 2011, 76, 1922.
10. (f) Gesinski, M. R.; Rychnovsky, S. D. J. Am. Chem. Soc. 2011, 133, 9727.
11. Kim, H.; Hong, J. Org. Lett. 2010, 12, 2880.
12. Carrick, J. D.; Jennings, M. P. Org. Lett. 2009, 11, 769.
13. Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C. J. Org. Chem. 1986, 51, 432.
14. (a) Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3, 1049.
15. (b) Smith, C. M.; O'Doherty, G. A. Org. Lett. 2003, 5, 1959.
16. (c) Guo, H.; Mortensen, M. S.; O'Doherty, G. A. Org. Lett. 2008, 10, 3149.
17. (a) Evans, D. A.; Gauchet-Prunet, J. A. J. Org. Chem. 1993, 58, 2446.
18. (b) Rotulo-Sims, D.; Prunet, J. Org. Lett. 2007, 9, 4147.
19. (a) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
20. (b) Reetz, M. T. Acc. Chem. Res. 1993, 26, 462.
21. Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G. J. Am. Chem. Soc. 1996, 118, 4322.
22. (a) Ding, F.; Jennings, M. P. Org. Lett. 2005, 7, 2321.
23. (b) Sawant, K. B.; Jennings, M. P. J. Org. Chem. 2006, 71, 7911.
24. (c) Sawant, K. B.; Ding, F.; Jennings, M. P. Tetrahedron Lett. 2006, 47, 939.
25. (d) Sawant, K. B.; Ding, F.; Jennings, M. P. Tetrahedron Lett. 2007, 48, 5177.
26. (e) Ding, F.; Jennings, M. P. J. Org. Chem. 2008, 73, 5965.
27. (f) Martinez-Solorio, D.; Jennings, M. P. J. Org. Chem. 2010, 75, 4095.
28. (a) Romero, J. A. C.; Tabacco, S. A.; Woerpel, K. A. J. Am. Chem. Soc. 2000, 122, 168.
29. (b) Ayala, L.; Lucero, C. G.; Romero, J. A. C.; Tabacco, S. A.; Woerpel, K. A. J. Am. Chem. Soc. 2003, 125, 15521.
30. (a) Lindgren, B. O.; Nilsson, T. Acta Chem. Scand. 1973, 27, 888.
31. (b) Kraus, G. A.; Taschner, M. J. J. Org. Chem. 1980, 45, 1175.
32. (c) Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825.
33. (d) Pinnick, H. W.; Childers, W. E.; Bal, B. S. Tetrahedron 1981, 37, 2091.
34. Yamaguchi, M. A.; Katsuki, T.; Sacki, H.; Hirata, K.; Inanaga, J. Bull. Chem. Soc. Jpn. 1979, 52, 1989.