Synthesis of balsaminone a, a naturally occurring pentacyclic dinaphthofuran quinone

Journal of Organic Chemistry

Volumn 76, Issue 19, 2011, Pages 8082-8087

  Padwal, Jalindar ^a   Lewis, William ^a   Moody, Christopher J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

METHOXY GROUP; NATURAL PRODUCTS; NATURALLY OCCURRING; STRUCTURAL ASSIGNMENTS;

ALDEHYDES; PHENOLS;

X RAY CRYSTALLOGRAPHY;

1,4 DIHYDROXY 2 NAPHTHALDEHYDE; 1,4 DIMETHOXY 2 NAPHTHALDEHYDE; 2 BROMO 1,4 DIMETHOXYNAPHTHALENE; 5 BENZYLOXY 6 HYDROXYDINAPHTHO[2,3 B:2',1' D]FURAN 7,12 DIONE; 5 BENZYLOXY 6 METHOXYDINAPHTHO[2,3 B:2',1' D]FURAN 7,12 DIONE; 5 BENZYLOXY 7,12 DIOXO 7,12 DIHYDRODINAPHTHO[2,3 B:2',1' D]FURAN 6 CARBALDEHYDE; 5 BENZYLOXY 7,12 DIOXO 7,12 DIHYDRODINAPHTHO[2,3 B:2',1' D]FURAN 6 YL FORMATE; 5 HYDROXY 7,12 DIOXO 7,12 DIHYDRODINAPHTHO[2,3 B:2',1' D]FURAN 6 CARBALDEHYDE; 6 ACETYL 5 (BENZYLOXY)DINAPHTHO[2,3 B:2',1' D]FURAN 7,12 DIONE; 6 ACETYL 5 HYDROXYDINAPHTHO[2,3 B:2',1' D]FURAN 7,12 DIONE; 6 METHOXY 7,12 DIOXO 7,12 DIHYDRODINAPHTHO[2,3 B:2',1' D]FURAN 5YL ACETATE; BALSAMINONE A; DINAPHTHOFURAN QUINONE; NATURAL PRODUCT; PENTACYCLIC TRITERPENE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

2 ACETYL 1,4 DIHYDROXYNAPHTHOQUINONE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DEMETHYLATION; IMPATIENS BALSAMINA; ISOLATION AND PURIFICATION; MEDICINAL PLANT; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BIOLOGICAL AGENTS; CHEMISTRY TECHNIQUES, SYNTHETIC; NAPHTHOQUINONES;

EID: 80054118278     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201395n     Document Type: Article

References (19)

1. Thomson, R. H. Naturally Occurring Quinones IV: Recent Advances, 4th ed.; Blackie: London, 1997.
2. Ishiguro, K.; Ohira, Y.; Oku, H. J. Nat. Prod. 1998, 61, 1126-1129.
3. MacKenzie, A. R.; Moody, C. J.; Rees, C. W. J. Chem. Soc., Chem. Commun. 1983, 1372-1373.
4. Davis, C. J.; Hurst, T. E.; Jacob, A. M.; Moody, C. J. J. Org. Chem. 2005, 70, 4414-4422.
5. McErlean, C.S. P.; Moody, C. J. J. Org. Chem. 2007, 72, 10298-10301.
6. Coombes, C. L.; Moody, C. J. J. Org. Chem. 2008, 73, 6758-6762.
7. Guillonneau, L.; Taddei, D.; Moody, C. J. Org. Lett. 2008, 10, 4505-4508.
8. Padwal, J.; Lewis, W.; Moody, C. J. Org. Biomol. Chem. 2011, 9, 3484-3493.
9. Smith, M. J.; Nawrat, C. C.; Moody, C. J. Org. Lett. 2011, 13, 3396-3398.
10. Liebermann, C. Chem. Ber. 1899, 32, 916-925.
11. Tandon, V. K.; Maurya, H. K. Tetrahedron Lett. 2009, 50, 5896-5902.
12. Sartori, M. F. Chem. Rev. 1963, 63, 279-&.
13. Cheng, C. C.; Dong, Q.; Liu, D. F.; Luo, Y. L.; Liu, L. F.; Chen, A. Y.; Yu, C.; Savaraj, N.; Chou, T. C. J. Med. Chem. 1993, 36, 4108-4112.
14. Lee, K. I.; Park, Y.; Park, S. J.; Hwang, J. H.; Lee, S. J.; Kim, G. D.; Park, W. K.; Lee, S.; Jeong, D.; Kong, J. Y.; Kang, H. K.; Cho, H. Bioorg. Med. Chem. Lett. 2006, 16, 737-742.
15. Boyer, J. L.; Krum, J. E.; Myers, M. C.; Fazal, A. N.; Wigal, C. T. J. Org. Chem. 2000, 65, 4712-4714.
16. Brimble, M. A.; Elliott, R. J. R. Tetrahedron 1997, 53, 7715-7730.
17. Fieser, L. F. J. Am. Chem. Soc. 1948, 70, 3165-3174.
18. Johnson, M. M.; Naidoo, J. M.; Fernandes, M. A.; Mmutlane, E. M.; van Otterlo, W. A. L.; de Koning, C. B. J. Org. Chem. 2010, 75, 8701-8704.
19. Nyland, R. L.; Luo, M. H.; Kelley, M. R.; Borch, R. F. J. Med. Chem. 2010, 53, 1200-1210.