Synthesis of benzodioxepanes

Tetrahedron

Volumn 68, Issue 31, 2012, Pages 6224-6230

  Chang, Meng Yang ^a   Wu, Ming Hao ^a   Lee, Tein Wei ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

Author keywords

Baeyer Villiger reaction; Benzodioxapane; Claisen rearrangement; O Allylation; ortho Metalation; Ring closing metathesis

Indexed keywords

4 METHOXY 3 HYDROXYBENZALDEHYDE; 7 METHOXY 10 METHYL 2,3,4,5,9,10,11,12 OCTAHYDRO 1,8 DIOXABENZO[1,2;3,4]DICYCLOHEPTENE; 7 METHOXY 2,3,4,5,9,10,11,12 OCTAHYDRO 1,8 DIOXABENZO[1,2;3,4]DICYCLOHEPTENE; 7 METHOXY 3,10 DIMETHYL 2,3,4,5,9,10,11,12 OCTAHYDRO 1,8 DIOXABENZO[1,2;3,4]DICYCLOHEPTENE; 7 METHOXY 5 METHYL 2,3,4,5,9,10,11,12 OCTAHYDRO 1,8 DIOXABENZO[1,2;3,4]DICYCLOHEPTENE; BENZALDEHYDE; BENZODIOXEPANE DERIVATIVE; OXEPANE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; BAEYER VILLIGER REACTION; CARBON NUCLEAR MAGNETIC RESONANCE; CLAISEN REARRANGEMENT; CRYSTAL STRUCTURE; HYDROGENATION; ONE POT SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS;

EID: 84862651933     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.05.063     Document Type: Article

References (43)

1. (a) Ellis, G. P. Chromenes, Chromanones, and Chromones. The Chemistry of Heterocyclic Compounds; Wiley: New York, NY, 1977; vol. 31, p 11;
2. (b) Hepworth, J. In; Katrizky, A. R., Rees, C. W., Eds. Comprehensive Heterocyclic Chemistry; Pergamon: Oxford, UK, 1984; vol. 3, p 737.
3. (a) Davis, M.; Pettett, M. Aust. J. Chem. 1979, 32, 369;
4. (b) Rustaiyan, A.; Nazarians, L.; Bohlmann, F. Phytochemistry 1980, 19, 1254;
5. (c) Kamperdick, C.; Van, N. H.; Sung, T. V.; Adam, G. Phytochemistry 1997, 45, 1049;
6. (d) Muyard, F.; Bissoue, A. N.; Bevalot, F.; Tillequin, F.; Cabalion, P.; Vaquette, J. Phytochemistry 1996, 42, 1175;
7. (e) Lee, Y. R.; Li, X. Bull. Korean Chem. Soc. 2007, 28, 1739.
8. (a) McKee, T.; Fuller, R. W.; Covington, C. D.; Cardellina, J. H., II; Gulakowski, R. J.; Krepps, B. L.; McMahon, J. B.; Boyd, M. R. J. Nat. Prod. 1996, 59, 754;
9. (b) Galinis, D. L.; Fuller, R. W.; McKee, T. C.; Cardellina, J. H., II; Gulakowski, R. J.; McMahon, J. B.; Boyd, M. R. J. Med. Chem. 1996, 39, 4507;
10. (c) Cardellina, J. H.; Bokesch, H. R.; McKee, T. C.; Boyd, M. R. Bioorg. Med. Chem. Lett. 1995, 5, 1011.
11. Tsai, J.-C.; Li, S.-R.; Chen, L.-Y.; Chen, P. Y.; Jhong, J. Y.; Shu, C.-J.; Lo, Y.-F.; Lin, C.-N.; Wang, E.-C. J. Chin. Chem. Soc. 2008, 55, 1317 and cited references therein.
12. (a) De Silva, S. O.; Watanabe, M.; Snieckus, V. J. Org. Chem. 1979, 44, 4802;
13. (b) Shih, T. L.; Wyvratt, M. J.; Mrozik, H. J. Org. Chem. 1987, 52, 2029;
14. (c) Snieckus, V. Chem. Rev. 1990, 90, 879;
15. (d) Rauer, W.; Schleyer, P. V. R. J. Am. Chem. Soc. 1989, 111, 7191;
16. (e) Stefinovic, M.; Snieckus, V. J. Org. Chem. 1998, 63, 2808;
17. (f) Lane, C.; Snieckus, V. Synlett 2000, 1294;
18. (g) Sibi, M. P.; Chattopadhyay, S.; Dankwardt, J. W.; Snieckus, V. J. Am. Chem. Soc. 1985, 107, 6312;
19. (h) Comins, D. L. Synlett 1992, 615;
20. (i) Le Fur, N.; Mojovic, L.; Ple, N.; Turck, A.; Reboul, V.; Metzner, P. J. Org. Chem. 2006, 71, 2609;
21. (j) Alessi, M.; Larkin, A. L.; Ogilvie, K. A.; Green, L. A.; Lai, S.; Lopez, S.; Snieckus, V. J. Org. Chem. 2007, 72, 1588;
22. (k) Chang, M.-Y.; Lee, N.-C. Synlett 2012, 867.
23. 2-mediated allylation.
24. For reviews on the ring-closing metathesis reaction, see: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446;
25. (b) Schmalz, H. G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833;
26. (c) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 2036;
27. (d) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 1., 371;
28. (e) Philips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75;
29. (f) Pandit, U. K.; Overkleeft, H. S.; Borer, B. C.; Bieraugel, H. Eur. J. Org. Chem. 1999, 5, 959;
30. (g) Wright, D. L. Curr. Org. Chem. 1999, 3, 75;
31. (h) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073;
32. (i) Felpin, F. X.; Lebreton, J. Eur. J. Org. Chem. 2003, 9, 3693;
33. (j) Cossy, J. Chem. Rec. 2005, 5, 70.
34. (a) Kato, H.; Ishigame, T.; Oshima, N.; Hoshiya, N.; Shimawaki, K.; Arisawa, M.; Shuto, S. Adv. Synth. Catal. 2011, 353, 2676;
35. (b) Tietze, L. F. Chem. Rev. 1996, 96, 195.
36. CCDC 865591 (1b) and 867570 (2c) contain the supplementary crystallographic data for this paper. This data can be obtained free of charge via www.ccdc.cam. ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: 44-1223-336033; e-mail: deposit@ccdc.cam.ac.uk).
37. For reviews on the Claisen rearrangement, see: (a) Castro, A. M. Chem. Rev. 2004, 104, 2939;
38. (b) Nubbemeyer, U. Synthesis 2003, 961;
39. (c) Hiersemann, M.; Abraham, L. Eur. J. Org. Chem. 2002, 1461;
40. (d) Chai, Y.; Hong, S.; Lindsay, H. A.; MaFarland, C.; McIntosh, M. C. Tetrahedron 2002, 58, 2905.
41. Chattopadhyay, S. K.; Biswas, T.; Maity, S. Synlett 2006, 2211.
42. Hong, S. H.; Sanders, D. P.; Lee, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2005, 127, 17160.
43. Wang, E. C.; Wang, C. C.; Hsu, M. K.; Huang, K. S. Heterocycles 2002, 57, 2021.