Absolute configuration of actinophyllic acid as determined through chiroptical data

Journal of Natural Products

Volumn 72, Issue 3, 2009, Pages 430-432

  Taniguchi, Tohru ^a,d   Martin, Connor L ^b   Monde, Kenji ^c   Nakanishi, Koji ^a   Berova, Nina ^a   Overman, Larry E ^b  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c HOKKAIDO UNIVERSITY   (Japan)

^d HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3,6,7,9,13C HEXAHYDRO 1H 1,7,8 (METHANETRIYLOXYMETHANO)PYRROLO[1',2':1,2]AZACINO[4,3 B]INDOLE 8(5H) CARBOXYLIC ACID; ACTINOPHYLLIC ACID; ALKALOID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ALSTONIA ACTINOPHYLLA; ARTICLE; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; DRUG ISOLATION; DRUG SYNTHESIS; ELECTRON; ENANTIOMER; MEDICINAL PLANT; OPTICAL ROTATION; RACEMIZATION;

ALKALOIDS; ALSTONIA; INDOLE ALKALOIDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STEREOISOMERISM;

ALSTONIA;

EID: 65249108138     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np800665s     Document Type: Article

References (27)

1. Carroll, A. R.; Hyde, E.; Smith, J.; Quinn, R. J.; Guymer, G.; Forster, P. I. J. Am. Chem. Soc. 2005, 70, 1096-1099.
2. Martin, C. L.; Overman, L. E.; Rohde, J. M. J. Am. Chem. Soc. 2008, 130, 7568-7569.
3. Stephens, P. J.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J. J. Phys. Chem., A 2001, 105, 5356-5371.
4. Polavarapu, P. L. Chirality 2002, 14, 768-781.
5. Giorgio, E.; Roje, M.; Tanaka, K.; Hamersak, Z.; Sunjik, V.; Nakanishi, K.; Rosini, C.; Berova, N. J. Org. Chem. 2005, 70, 6557-6563.
6. Stephens, P. J.; Pan, J. J.; Devlin, F. J.; Cheeseman, J. R. J. Nat. Prod. 2008, 71, 285-288.
7. Diederich, C.; Grimme, S. J. Phys. Chem., A 2003, 107, 2524-2539.
8. Schuhly, W.; Crochett, S. L.; Fabian, W. M. F. Chirality 2005, 17, 250-256.
9. Hussain, H.; Krohn, K.; Floerke, U.; Schulz, B.; Draeger, S.; Pescitelli, G.; Antus, S.; Kurtan, T. Eur. J. Org. Chem. 2007, 72, 292-295.
10. Ding, Y.; Li, X.-C.; Ferreira, D. J. Org. Chem. 2007, 72, 9010-9017.
11. Cheeseman, J. R.; Frisch, M. J.; Devlin, F. J.; Stephens, P. J. Chem. Phys. Lett. 1996, 252, 211-220.
12. Freedman, T. B.; Cao, X.; Dukor, R. K.; Nafie, L. A. Chirality 2003, 15, 743-758.
13. Monde, K.; Taniguchi, T.; Miura, M.; Vairappan, C. S.; Suzuki, M. Tetrahedron Lett. 2006, 47, 4389-4392.
14. Cerda-Garcia-Rojas, C. M.; Catalan, C. A. N.; Muro, A. C.; Joseph- Nathan, P. J. Nat. Prod. 2008, 71, 967-971.
15. Stephens, P. J.; McCann, D. M.; Devlin, F. J.; Smith, A. B. J. Nat. Prod. 2006, 69, 1055-1064.
16. Polavarapu, P. L. Chem. Rec. 2007, 7, 125-136.
17. Polavarapu, P. L. Chirality 2008, 20, 664-672.
18. Schlingmann, G.; Taniguchi, T.; Haiyin, H.; Bigelis, R.; Yang, H. Y.; Koehn, F. E.; Carter, G. T.; Berova, N. J. Nat. Prod. 2007, 70, 1180-1187.
19. Taniguchi, T.; Monde, K.; Nakanishi, K.; Berova, N. Org. Biomol. Chem. 2008, 6, 4399-4405.
20. He, J.; Wang, F.; Polavarapu, P. L. Chirality 2005, 17,S1-S8.
21. Devlin, F. J.; Stephens, P. J.; Bortolini, O. Tetrahedron: Asymmetry 2005, 16, 2653-2663.
22. Kuppens, T.; Herreboout, W.; van der Veken, B.; Bultinck, P. J. Phys. Chem., A 2006, 110, 10191-10200.
23. Nafie, L. A. Nat. Prod. Commun. 2008, 3, 451-466.
24. Burgueño-Tapia, E.; Joseph-Nathan, P. Phytochierriistry 2008, 69, 2251-2256.
25. Stephens, P. J.; McCann, D. M.; Cheeseman, J. R.; Frisch, M. J. Chirality 2005, 17, S52-S64.
26. 1H NMR spectrum reported for natural product 1.
27. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy-exciton coupling in organic stereochemistry; University Science Books: Mill Valley, CA, 1983.