Synthesis of the reported structure of the bisbenzoquinone lanciaquinone, isolated from Maesa lanceolata

Organic Letters

Volumn 10, Issue 20, 2008, Pages 4505-4508

  Guillonneau, Loic ^a   Taddei, David ^a   Moody, Christopher J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE; BENZOQUINONE DERIVATIVE; LANCIAQUINONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOLATION AND PURIFICATION; MYRSINACEAE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

BENZOQUINONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; MYRSINACEAE;

EID: 58149150979     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801697g     Document Type: Article

References (24)

1. Thomson, R. H. Naturally Occurring Quinones, 2nd ed.; Academic Press: London, 1971.
2. Thomson, R. H. Naturally Occurring Quinones III. Recent advances, 3rd ed.; Chapman and Hall: London, 1987.
3. Thomson, R. H. Naturally Occurring Quinones IV. Recent advances, 4th ed.; Blackie: London, 1997.
4. Ogawa, H.; Natori, S. Chem. Pharm. Bull. 1968, 16, 1709-1720.
5. Yang, L. K.; Khoo-Beattie, C.; Goh, K. L.; Chng, B. L.; Yoganathan, K.; Lai, Y. H.; Butler, M. S. Phytochemistry 2001, 58, 1235-1238.
6. Manguro, L. O. A.; Midiwo, J. O.; Kraus, W.; Ugi, I. Phytochemistry 2003, 64, 855-862.
7. McErlean, C. S. P.; Moody, C. J. J. Org. Chem. 2007, 72, 10298-10301.
8. McErlean, C. S. P.; Sperry, J.; Blake, A. J.; Moody, C. J. Tetrahedron 2007, 63, 10963-10970.
9. Colucci, M. A.; Couch, G. D.; Moody, C. J. Org. Biomol. Chem. 2008, 6, 637-656.
10. Davis, C. J.; Moody, C. J. Synlett 2002, 1874-1876.
11. Davis, C. J.; Hurst, T. E.; Jacob, A. M.; Moody, C. J. J. Org. Chem. 2005, 70, 4414-4422.
12. Jacob, A. M.; Moody, C. J. Tetrahedron Lett. 2005, 46, 8823-8825.
13. For other uses of double Claisen rearrangements in different contexts, see the following and refs 14-19: Hiratani, K.; Takahashi, T.; Kasuga, K.; Sugihara, H.; Fujiwara, K.; Ohashi, K. Tetrahedron Lett. 1995, 36, 5567-5570.
14. Tisdale, E. J.; Vong, B. G.; Li, H. M.; Kim, S. H.; Chowdhury, C.; Theodorakis, E. A. Tetrahedron 2003, 59, 6873-6887.
15. Kotha, S.; Mandal, K. Tetrahedron Lett. 2004, 45, 2585-2588.
16. Kotha, S.; Mandal, K.; Deb, A. C.; Banerjee, S. Tetrahedron Lett. 2004, 45, 9603-9605.
17. Chattopadhyay, S. K.; Biswas, T.; Maity, S. Synlett 2006, 2211-2214.
18. Kotha, S.; Dipak, M. K. Chem. - Eur. J. 2006, 12, 4446-1450.
19. Nicolaou, K. C.; Lister, T.; Demon, R. M.; Gelin, C. F. Angew. Chem., Int. Ed. 2007, 46, 7501-7505.
20. Trost, B. M.; Kulawiec, R. J. J. Am. Chem. Soc. 1993, 115, 2027-2036.
21. DeJong, C. R. H. I.; Hageman, H. J.; Hoentjen, G.; Mus, W. J. Org. Synth. 1988, 6, 412-413.
22. Parker, K. A.; Taveras, D. In Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons Ltd: Chichester, 1995; Vol. 6, pp 4423-4425.
23. Sontag, B.; Dasenbrock, J.; Arnold, N.; Steglich, W. Eur. J. Org. Chem. 1999, 1051-1055.
24. Rukachaisirikul, V.; Kamkaew, M.; Sukavisit, D.; Phongpaichit, S.; Sawangchote, P.; Taylor, W. C. J. Nat. Prod. 2003, 66, 1531-1535.