The viability of nitrone-alkene (3 + 2) cycloadditions in alkaloid biosynthesis

Journal of Organic Chemistry

Volumn 79, Issue 1, 2014, Pages 432-435

  Painter, Phillip P ^a   Pemberton, Ryan P ^a   Wong, Bonnie M ^a   Ho, Krystina C ^a   Tantillo, Dean J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[4 + 2] CYCLOADDITION; ALKALOID BIOSYNTHESIS; CYCLOADDITION REACTION; CYCLOADDITIONS; DIASTEREO-SELECTIVITY; INTRINSIC BARRIERS; NATURAL PRODUCTS;

ALKALOIDS; BIOCHEMISTRY; CYCLOADDITION; HYDROCARBONS; METABOLITES; NITROGEN COMPOUNDS;

BIOSYNTHESIS;

ALKALOID DERIVATIVE; ALKENE DERIVATIVE; NITRONE DERIVATIVE;

ARTICLE; BIOSYNTHESIS; CALCULATION; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; DIASTEREOISOMER; QUANTUM CHEMISTRY; STEREOCHEMISTRY;

ALKALOIDS; ALKENES; BIOLOGICAL PRODUCTS; CYCLOADDITION REACTION; MOLECULAR STRUCTURE; NITROGEN OXIDES; QUANTUM THEORY; STEREOISOMERISM;

EID: 84891694750     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402487d     Document Type: Article

References (30)

1. Kelly, W. L. Org. Biomol. Chem. 2008, 6, 4483-4493
2. Stocking, E. M.; Williams, R. M. Angew. Chem., Int. Ed. 2003, 42, 3078-3115
3. Oikawa, H. Bull. Chem. Soc. Jpn. 2005, 78, 537-554
4. Oikawa, H.; Tokiwano, T. Nat. Prod. Rep. 2004, 21, 321-352
5. Pohnert, G. ChemBioChem 2001, 12, 873-875
6. Roethle, P. A.; Hernandez, P. T.; Trauner, D. Org. Lett. 2006, 8, 5901-5904
7. Tang, B.; Bray, C. D.; Pattenden, G. Tetrahedron Lett. 2006, 47, 6401-6404
8. Wang, S. C.; Tantillo, D. J. J. Org. Chem. 2008, 73, 1516-1523
9. Wang, G.; Liang, J.; Wang, Y.; Li, Q.; Ye, W. J. Nat. Med. 2008, 6, 251-253
10. Wang, G.; Wang, Y.; Li, Q.; Liang, J.; Zhang, X.; Yao, X.; Ye, W. Helv. Chim. Acta 2008, 91, 1124-1129
11. Zhao, B.; Wang, Y.; Zhang, D.; Jiang, R.; Wang, G.; Shi, J.; Huang, X.; Chen, W.; Che, C.; Ye, W. Org. Lett. 2011, 13, 3888-3891
12. Zhao, B.; Wang, Y.; Zhang, D.; Huang, X.; Bai, L.; Yan, Y.; Chen, J.; Lu, T.; Wang, Y.; Zhang, Q. Org. Lett. 2012, 14, 3096-3099
13. Wei, H.; Qiao, C.; Liu, G.; Yang, Z.; Li, C. Angew. Chem., Int. Ed. 2013, 52, 620-624
14. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 50, 215-241
15. Frisch, M. J.; Gaussian 09, revision A.02; Gaussian, Inc.; Wallingford, CT, 2009.
16. Linder, M.; Brinck, T. Phys. Chem. Chem. Phys. 2013, 15, 5108-5114
17. Krenske, E. H.; Agopcan, S.; Aviyente, V.; Houk, K. N.; Johnson, B. A.; Holmes, A. B. J. Am. Chem. Soc. 2012, 134, 12010-12015
18. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527
19. Fukui, K. Acc. Chem. Res. 1981, 14, 363-368
20. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378-6396
21. Müller, N.; Faulk, A.; Gsaller, G. Ball & Stick Molecular Graphics, Application for MacOS Computers, version 4.0a12; Johannes Kepler University: Linz, Austria, 2004.
22. Shao, Y. Phys. Chem. Chem. Phys. 2006, 8, 3172-3191
23. Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 10646-10647
24. Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2008, 130, 10187-10198
25. Hayden, A. E.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 4084-4089
26. Lopez, S. A.; Houk, K. N. J. Org. Chem. 2012, 78, 1778-1783
27. van Zeist, W.; Bickelhaupt, F. M. Org. Biomol. Chem. 2010, 8, 3118-3127
28. Fernández, I.; Bickelhaupt, F. M.; Cossío, F. P. Chem.-Eur. J. 2012, 18, 12395-12403
29. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO 3.0; University of Wisconsin, Madison, WI. This approach makes use of second-order perturbation theory.
30. After the original submission of this manuscript, a related study was published. See: Krenske, E. H.; Patel, A.; Houk, K. N. J. Am. Chem. Soc. 2013, 10.1021/ja409928z