Case study of empirical and computational chemical shift analyses: Reassignment of the relative configuration of phomopsichalasin to that of Diaporthichalasin

Journal of Natural Products

Volumn 75, Issue 7, 2012, Pages 1326-1331

  Brown, Susan G ^a   Jansma, Matthew J ^a   Hoye, Thomas R ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; DIAPORTHICHALASIN; PHOMOPSICHALASIN; UNCLASSIFIED DRUG;

ARTICLE; DENSITY FUNCTIONAL THEORY; DIASTEREOISOMER; DRUG ISOLATION; DRUG STRUCTURE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

ASCOMYCOTA; CYTOCHALASINS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR;

EID: 84864188375     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np300248w     Document Type: Article

References (17)

1. Horn, W. S.; Simmonds, M. S. J.; Schwartz, R. E.; Blaney, W. M. Tetrahedron 1995, 51, 3969-3978
2. Pornpakakul, S.; Roengsumran, S.; Deechangvipart, S.; Petsom, A.; Muangsin, N.; Ngamrojnavanich, N.; Sriubolmas, N.; Chaichit, N.; Ohta, T. Tetrahedron Lett. 2007, 48, 651-655
3. Dalling, D. K.; Curtis, J.; Grant, D. M. J. Org. Chem. 1986, 51, 136-142
4. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
5. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157-167
6. Wiitala, K. W.; Hoye, T. R.; Cramer, C. J. J. Chem. Theory Comput. 2006, 2, 1085-1092
7. Use of the WP04 functional for the computation of accurate proton chemical shifts has recently been advocated; see: Jain, R.; Bally, T.; Rablen, P. R. J. Org. Chem. 2009, 74, 4017-4023
8. Jensen, F. J. Chem. Theory Comput. 2008, 4, 719-727
9. Braddock, D. C.; Rzepa, H. S. J. Nat. Prod. 2008, 71, 728-730
10. Timmons, C.; Wipf, P. J. Org. Chem. 2008, 73, 9168-9170
11. Smith, S. G.; Goodman, J. M. J. Am. Chem. Soc. 2010, 132, 12946-12959
12. Paterson, I.; Dalby, S. M.; Roberts, J. C.; Naylor, G. J.; Guzmán, E. A.; Isbrucker, R.; Pitts, T. P.; Linley, P.; Divlianska, D.; Reed, J. K.; Wright, A. E. Angew. Chem., Int. Ed. 2011, 50, 3219-3223
13. Lodewyk, M. W.; Tantillo, D. J. J. Nat. Prod. 2011, 74, 1339-1343
14. Wyche, T. P.; Hou, Y.; Braun, D.; Cohen, H. C.; Xiong, M. P.; Bugni, T. S. J. Org. Chem. 2011, 76, 6542-6547
15. http://www-jmg.ch.cam.ac.uk/tools/nmr/DP4/.
16. Banfi, L.; Andrea, B.; Francesco, C.; Giuseppe, G.; Naz, F.; Riva, R.; Zitoa, P. Synlett 2010, 85-88
17. Gunawan, S.; Nichol, G. S.; Chappeta, S.; Dietrich, J.; Hulme, C. Tetrahedron Lett. 2010, 51, 4689-4692