Structure assignment of lagunapyrone B by fluorous mixture synthesis of four candidate stereoisomers

Journal of the American Chemical Society

Volumn 128, Issue 43, 2006, Pages 14200-14205

  Yang, Fanglong ^a   Newsome, Jeffery J ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COUPLINGS; OPTICAL ROTATION; SAMPLED DATA CONTROL SYSTEMS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

LAGUNAPYRONE; MIXTURE SYNTHESIS; NEGISHI COUPLING; QUASIRACEMIC MIXTURE; STEREOISOMERS;

ISOMERS;

FLUORINE; IODINE DERIVATIVE; LAGUNAPYRONE B; NATURAL PRODUCT; PYRONE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; OPTICAL ROTATION; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOISOMERISM; STILLE REACTION; STRUCTURE ANALYSIS; SYNTHESIS;

ALKENES; MOLECULAR STRUCTURE; PYRONES; STEREOISOMERISM;

EID: 33750457999     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja064812s     Document Type: Article

References (38)

1. Lindell, T.; Jenson, P. R.; Fenical, W. Tetrahedron Lett. 1996, 37, 1327-1330.
2. Rychnovsky, S. D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9-17.
3. Piericidins coexist with the lagunapyrones and have some structural resemblance. See: (a) Schnermann, M. J.; Boger, D. L. J. Am. Chem. Soc. 2005, 127, 15704-15705.
4. (b) Keaton, K. A.; Phillips, A. J. Am. Chem. Soc. 2006, 128, 408-409.
5. Luo, Z. Y.; Zhang, Q. S.; Oderaotoshi, Y.; Curran, D. P. Science 2001, 291, 1766-1769.
6. Short review: Zhang, W. Arkivoc 2004, 101-109.
7. (a) Zhang, Q. S.; Lu, H. J.; Richard, C.; Curran, D. P. J. Am. Chem. Soc. 2004, 126, 36-37.
8. (b) Dandapani, S.; Jeske, M.; Curran, D. P. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12008-12012.
9. (c) Dandapani, S.; Jeske, M.; Curran, D. P. J. Org. Chem. 2005, 70, 9447-9462.
10. (d) Wilcox, C. S.; Gudipati, V.; Lu, H. J.; Turkyilmaz, S.; Curran, D. P. Angew. Chem., Int. Ed. 2005, 44, 6938-6940.
11. (e) Fukui, Y.; Brückner, A. M.; Shin, Y.; Balachandran, R.; Day, B. W.; Curran, D. P. Org. Lett. 2006, 8, 301-304.
12. (f) Curran, D. P.; Moura-Letts, G.; Pohlman, M. Angew. Chem., Int. Ed. 2006, 45, 2423-2426.
13. (g) Curran, D. P.; Zhang, Q.; Richard, C.; Lu, H.; Gudipati, V.; Wilcox, C. W. J. Am. Chem. Soc. 2006, 128, 9567-9573.
14. (h) Curran, D. P.; Zhang, Q.; Lu, H.; Gudipati, V. J. Am. Chem. Soc. 2006, 128, 9943-9956.
15. (a) Zhang, Q. S.; Rivkin, A.; Curran, D. P. J. Am. Chem. Soc. 2002, 124, 5774-5781.
16. (b) Zhang, Q. S.; Curran, D. P. Chem.-Eur. J. 2005, 11, 4866-4880.
17. (a) Negishi, E.; Hu, Q.; Huang, Z. H.; Qian, M. X.; Wang, G. W. Aldrichimica Acta 2005, 38, 71-88.
18. (b) Huo, S.; Negishi, E.-i. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 1. pp 335-408.
19. Farina, V.; Krishnamurthy, V.; Scott, W. L. Org. React. 1997, 50, 1-652.
20. (a) Paterson, I.; Wallace, D. J.; Cowden, C. J. Synthesis 1998, 639-652.
21. (b) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1-200.
22. (a) Zhang, W.; Luo, Z.; Chen, C. H. T.; Curran, D. P. J. Am. Chem. Soc. 2002, 124, 10443-10450.
23. (b) Fluorous silanes and silica products were purchased from Fluorous Technologies, Inc. DPC owns an equity interest in this company.
24. (a) Makabe, H.; Higuchi, M.; Konno, H.; Murai, M.; Miyoshi, H. Tetrahedron Lett. 2005, 46, 4671-4674.
25. (b) Sinha, S.; Sinha-Bagchi, A.; Keinan, E. J. Org. Chem. 1993, 58, 7789-7796.
26. Afarinka, K.; Vindev, V. Sci. Synth. 2003, 14, 275-346.
27. Yang, F. Ph.D. Thesis, University of Pittsburgh, 2006.
28. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405-4408.
29. Nakajima, N.; Abe, R.; Yonemistu, O. Chem. Pharm. Bull. 1988, 36, 4244.
30. (a) Evans, D. A.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc. 1981, 103, 3099-3111.
31. (b) Evans, D. A.; Reiger, D. L.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc. 1991, 113, 1047-1049.
32. Makino, K.; Henmi, Y.; Hamada, Y. Synlett 2002, 613-615.
33. Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894-902.
34. Evans, D. A.; Allison, B. D.; Yang, M. G.; Masse, C. E. J. Am. Chem. Soc. 2001, 123, 10840-10852.
35. This sequence of steps was also conducted with a TBS protecting group, and this is described in ref 14 and in the Supporting Information.
36. Wipf, P.; Lim, S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1095-1097.
37. Curran, D. P. In The Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horvath, I. T., Eds.; Wiley-VCH: Weinheim, 2004; pp 101-127.
38. D = -11.4 at c = 0.4. We thank Mr. X. Wang for conducting these experiments.