Total synthesis of moracin C

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 20, 1998, Pages 3453-3457

  McAllister, Graeme D ^a   Hartley, Richard C ^a   Dawson, Michael J ^b   Knaggs, Andrew R ^b  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748509325     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a805026k     Document Type: Article

References (32)

1. M. Takasugi, S. Nagao, S. Ueno, T. Masamune, A. Shirata and K. Takahashi, Chem. Lett., 1978, 1239.
2. S. Matsuyama, Y. Kuwahara, S. Nakamura and T. Suzuki, Agric. Biol. Chem., 1991, 55, 1333.
3. Y. Hano, A. Ayukawa, T. Nomura and S. Ueda, J. Am. Chem. Soc., 1994, 116, 4189 and references 1-4 therein.
4. I. S. Mann and D. A. Widdowson, Tetrahedron, 1991, 47, 7991.
5. I. S. Mann and D. A. Widdowson, Tetrahedron, 1991, 47, 7981.
6. A. Hercouet and M. Le Corre, Tetrahedron, 1981, 37, 2867;
7. A. Hercouet and M. Le Corre, Tetrahedron Lett., 1979, 2145.
8. B. A. McKittrick and R. Stevenson, J. Chem. Soc., Perkin Trans. 1, 1984, 709.
9. T. Malkin and M. Nierenstein, J. Am. Chem. Soc., 1931, 53, 239.
10. Reaction of aldehyde 15 using 1 equivalent of acetic anhydride gave a 1:3:1 mixture of aldehyde 15, 4-acetoxy-2-hydroxybenzaldehyde and diacetate 23; L. Noble and R. C. Hartley, unpublished results.
11. G. Nicolosi, M. Piattelli and C. Sanfilippo, Tetrahedron, 1993, 49, 3143.
12. R. J. K. Taylor, Organocopper Reagents A Practical Approach, Oxford University Press, Oxford, 1994, 113.
13. V. G. S. Box and D. P. Brown, Heterocycles, 1991, 32, 1273;
14. G. Ferguson, B. L. Ruhl, J. Gilmore, T. Ibrahim and W. B. Whalley, J. Chem. Res. (M), 1985, 3101;
15. S. Arcamone, G. Cassinelli, F. DiMatteo, S. Forenza, M. C. Ripamonti, G. Rivola, A. Vigevani, J. Clardy and T. McCabe, J. Am. Chem. Soc., 1980, 102, 1462.
16. M. Watanabe, K. Kawanishi and S. Furukawa, Chem. Pharm. Bull., 1991, 39, 579.
17. Other examples that illustrate different methods for the synthesis of phenolic 2-arylbenzo[b]furans: T. Kinoshita, Tetrahedron Lett., 1997, 38, 259;
18. T. A. Engler and W. Chai, Tetrahedron Lett., 1996, 37, 6969;
19. J. F. Cameron, C. G. Willson and J. M. J. Fréchet, J. Chem. Soc., Chem. Commun., 1995, 923;
20. R. C. Larock, E. K. Yum, M. J. Doty and K. K. C. Sham, J. Org. Chem., 1995, 60, 3270 (only applied to 2-phenylbenzo[b]furan) and references 8 and 9 therein;
21. O. Fujimura, G. C. Fu and R. H. Grubbs, J. Org. Chem., 1994, 59, 4029;
22. M. N. Kanvinde, R. M. Kelkar and M. V. Paradkar, Synth. Commun., 1993, 23, 961;
23. Z. Yang, H. B. Liu, C. M. Lee, H. M. Chang and H. N. C. Wong, J. Org. Chem., 1992, 57, 7248;
24. M. Barbier, Liebigs Ann. Chem., 1991, 393;
25. A. Clerici, O. Porta and A. Arnone, J. Org. Chem., 1990, 55, 1240;
26. J. Guillaumel, N. Boccara, P. Demerseman, R. Royer, J. P. Bideau, M. Cotrait and N. Platzer, J. Heterocycl. Chem., 1990, 27, 605;
27. G. Pandey, A. Krishna and U. T. Bhalerao, Tetrahedron Lett., 1989, 30, 1867;
28. T. Ota, S. Hasegawa, S. Inoue and K. Sato, J. Chem. Soc., Perkin Trans. 1, 1988, 3029;
29. B. Ledoussal, A. Gorgues and A. Le Coq, Tetrahedron, 1987, 43, 5841;
30. A. Arcadi, F. Marinelli and S. Cacchi, Synthesis, 1986, 749.
31. C. Deschamps-Vallet, J.-B. Ilotse, M. Meyer-Dayan and D. Mohlo, Tetrahedron Lett., 1979, 1109.
32. T. Kimachi, K. Tanaka and F. Yoneda, J. Heterocycl. Chem., 1991, 28, 439.