(±)-trans, cis -4-Hydroxy-5,6-di-O -isopropylidenecyclohex-2-ene-1- one: Synthesis and facile dimerization to decahydrodibenzofurans

Journal of Organic Chemistry

Volumn 76, Issue 5, 2011, Pages 1483-1486

  Paddock, Victoria L ^a   Phipps, Robert J ^a   Conde Angulo, Almudena ^a   Blanco Martin, Araceli ^a   Giró Mañas, Carles ^a   Martin, Laetitia J ^a   White, Andrew J P ^a   Spivey, Alan C ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXADIENES; EFFICIENT SYNTHESIS; HYDROXY GROUPS; PHOTOOXYGENATIONS;

DIMERIZATION;

BENZOFURAN DERIVATIVE; CATECHOL DERIVATIVE; CYCLOHEXANONE DERIVATIVE; HYDROXYL GROUP;

ADDITION REACTION; ARTICLE; CRYSTAL STRUCTURE; DIASTEREOISOMER; DIMERIZATION; PHOTOOXIDATION; STEREOCHEMISTRY; SYNTHESIS;

BENZOFURANS; CYCLOHEXENES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79952140369     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102314w     Document Type: Article

References (35)

1. For leading references to previous syntheses of lycorine and regarding its biological activity, respectively, see: Jones, M. T.; Schwartz, B. D.; Willis, A. C.; Banwell, M. G. Org. Lett. 2009, 11, 3506
2. Hayden, R. E.; Pratt, G.; Drayson, M. T.; Bunce, C. M. Haematologica 2010, 95, 1889-1896
3. Spivey, A. C.; Giró-Mañas, C.; Mann, I. Chem. Commun. 2005, 4426-4428
4. Johnson, C. R.; Adams, J. P.; Collins, M. A. J. Chem. Soc., Perkin Trans. 1 1993, 1-2
5. Johnson, C. R.; Ple, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006-1007
6. Dumortier, L.; Liu, P.; Dobbelaere, S.; Van der Eycken, J.; Vandewalle, M. Synlett 1992, 243-245
7. Mereyala, H. B.; Gaddam, B. R. J. Chem. Soc., Perkin Trans. 1 1994, 2187-2190
8. Katoh, T.; Izuhara, T.; Yokota, W.; Inoue, M.; Watanabe, K.; Nobeyama, A.; Suzuki, T. Tetrahedron 2006, 62, 1590-1608
9. Izuhara, T.; Katoh, T. Tetrahedron Lett. 2000, 41, 7651-7655
10. Wang, Z.-X.; Miller, S. M.; Anderson, O. P.; Shi, Y. J. Org. Chem. 1999, 64, 6443-6458
11. Hudlicky, T.; Luna, H.; Olivo, H. F.; Andersen, C.; Nugent, T.; Price, J. D. J. Chem. Soc., Perkin Trans. 1 1991, 2907-2917
12. Hudlicky, T.; Fan, R. L.; Tsunoda, T.; Luna, H.; Andersen, C.; Price, J. D. Isr. J. Chem. 1991, 31, 229-238
13. Oppolzer, W.; Spivey, A. C.; Bochet, C. G. J. Am. Chem. Soc. 1994, 116, 3139-3140
14. Banwell, M. G.; De Savi, C.; Hockless, D. C. R.; Pallich, S.; Watson, K. G. Synlett 1999, 885-888
15. Boyd, D. R.; Sharma, N. D.; Belhocine, T.; Malone, J. F.; McGregor, S.; Allen, C. C. R. Chem. Commun. 2006, 4934-4936
16. Hudlicky, T.; Gonzalez, D.; Gibson, D. T. Aldrichimica Acta 1999, 32, 35-62
17. Balci, M. Pure. Appl. Chem. 1997, 69, 97-104
18. Sutbeyaz, Y.; Secen, H.; Balci, M. J. Chem. Soc., Chem. Commun. 1988, 1330-1331
19. Secen, H.; Gultekin, S.; Sutbeyaz, Y.; Balci, M. Synth. Commun. 1994, 24, 2103-2108
20. Kornblum, N.; De La Mare, H. E. J. Am. Chem. Soc. 1951, 73, 880-881
21. It is possible that, by applying the organocatalytic, asymmetric Kornblum-DeLaMare rearrangement protocol developed by Toste et al. to endoperoxide 2, this synthesis could be rendered enantioselective; see: Staben, S. T.; Linghu, X.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 12658
22. Yang, N. C.; Chen, M.-J.; Chen, P. J. Am. Chem. Soc. 1984, 106, 7310-7315
23. Yang, N. C.; Chen, M. J.; Chen, P.; Mak, K. T. J. Am. Chem. Soc. 1982, 104, 853-855
24. The Chan sequence of reactions (ref 21) has been reported by Johnson et al. to proceed in 87% overall yield. In our hands, however, the original yields are reproduced; see: Johnson, C. R.; Ple, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006
25. Fabris, F.; Rosso, E.; Paulon, A.; De Lucchi, O. Tetrahedron Lett. 2006, 47, 4835-4837
26. The Fabris route (ref 24) is based on one developed by Mereyala for the synthesis of the cyclohexylidene analogue; see: Mereyala, H. B.; Pannala, M. Tetrahedron Lett. 1995, 36, 2121
27. Schenck, G. O.; Dunlap, D. E. Angew. Chem. 1956, 68, 248-249
28. Kaneko, C.; Sugimoto, A.; Tanaka, S. Synthesis 1974, 876-877
29. Boyd, J. D.; Foote, C. S.; Imagawa, D. K. J. Am. Chem. Soc. 1980, 102, 3641-3642
30. Ciaccio, J. A.; Heller, E.; Talbot, A. Synlett 1991, 248-250
31. 2 at -70 °C and a crystal structure reported; see: Han, X.; Khedekar, R. N.; Masnovi, J.; Baker, R. J. J. Org. Chem. 1999, 64, 5245-5250
32. 1H NMR following attempted isolation. However, this is only a minor component of the decomposition pathway in those reactions; the major decomposition product is highly polar and results from reaction of the enone 3 with the thiourea (or derived carbodiimide) employed to affect the final endoperoxide hydrogenolysis.
33. Carreno, M. C.; Ribagorda, M. Org. Lett. 2003, 5, 2425-2428
34. Suzuki, M.; Ohtake, H.; Kameya, Y.; Hamanaka, N.; Noyori, R. J. Org. Chem. 1989, 54, 5292-5302
35. Ramesh, K.; Wolfe, M. S.; Lee, Y.; Velde, D. V.; Borchardt, R. T. J. Org. Chem. 1992, 57, 5861-5868