Synthesis of the reported structure of crassiflorone, a pentacyclic naphthoquinone isolated from the African ebony diospyros crassiflora

Synlett

Volumn , Issue 4, 2010, Pages 514-516

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

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Copper; Diels Alder reaction; Fused ring systems; Natural products; Quinones

Indexed keywords

2 BROMO 8 HYDROXY 6 METHYLNAPHTHOQUINONE; CRASSIFLORONE; NAPHTHALENE DERIVATIVE; NAPHTHOQUINONE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DIELS ALDER REACTION; DIOSPYROS CRASSIFLORA; NONHUMAN; PERSIMMON; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 77955378768     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218578     Document Type: Article

References (16)

1. (a) Thomson, R. H. Naturally Occurring Quinones; Butterworths: London, 1957.
2. (b) Thomson, R. H. Naturally Occurring Quinones, 2nd ed.; Academic Press: London, 1971.
3. (c) Thomson, R. H. Naturally Occurring Quinones III. Recent Advances, 3rd ed.; Chapman and Hall: London, 1987.
4. (d) Thomson, R. H. Naturally Occurring Quinones IV. Recent Advances, 4th ed.; Blackie: London, 1997.
5. Tangmouo, J. G.; Meli, A. L.; Komguem, J.; Kuete, V.; Ngounou, F. N.; Lontsi, D.; Beng, V. P.; Choudhary, M. I.; Sondengam, B. L. Tetrahedron Lett. 2006, 47, 3067.
6. Kuete, V.; Tangmouo, J. G.; Meyer, J. J. M.; Lall, N. Int. J. Antimicrob. Agents 2009, 34, 322.
7. Savard, J.; Brassard, P. Tetrahedron 1984, 40, 3455.
8. Perumal, P. T.; Bhatt, M. V. Synthesis 1979, 205.
9. Bringmann, G.; Gotz, R.; Keller, P. A.; Walter, R.; Boyd, M. R.; Lang, F. R.; Garcia, A.; Walsh, J. J.; Tellitu, I.; Bhaskar, K. V.; Kelly, T. R. J. Org. Chem. 1998, 63, 1090.
10. Appendino, G.; Cravotto, G.; Giovenzana, G. B.; Palmisano, G. J. Nat. Prod. 1999, 62, 1627.
11. For some recent examples, see: Bolognesi, M. L.; Lizzi, F.; Perozzo, R.; Brun, R.; Cavalli, A. Bioorg. Med. Chem. Lett. 2008, 18, 2272.
12. Luly, J. R.; Rapoport, H. J. Am. Chem. Soc. 1983,105, 2859.
13. Murphy, W.S.; O'Sullivam, P. J. Tetrahedron Lett. 1992, 33, 531.
14. 2), 22.5 (Me), 21.5 (Me).
15. 3): δ = 177.7 (C), 177.3 (C), 162.83 (C), 162.80 (C), 155.1 (C), 154.7 (C), 152.9 (C), 149.4 (C), 136.0 (C), 133.2 (C), 133.1 (CH), 127.3 (CH), 127.2 (C), 124.7 (CH), 122.5 (CH), 115.4 (CH), 112.4 (C), 110.5 (C), 107.9 (C), 22.4 (Me), 21.4 (Me).
16. Crystallographic data (reference number CCDC 75266) can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB21EZ, UK; fax: +44 (1223) 336033; ordeposit@ccdc.cam.ac.uk].