Synthetic studies directed toward dideoxy lomaiviticinone lead to unexpected 1,2-oxazepine and isoxazole formation

Organic Letters

Volumn 14, Issue 4, 2012, Pages 1027-1029

  Baranczak, Aleksandra ^a   Sulikowski, Gary A ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE; BENZOQUINONE DERIVATIVE; CYCLOHEXANONE DERIVATIVE; DIDEOXY LOMAIVITICINONE; ISOXAZOLE DERIVATIVE; OXAZEPINE DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

BENZOQUINONES; CATALYSIS; CYCLOHEXANONES; ISOXAZOLES; MOLECULAR STRUCTURE; OXAZEPINES; OXIDATION-REDUCTION; POLYCYCLIC COMPOUNDS;

EID: 84857202761     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol203390w     Document Type: Article

References (27)

1. He, H.; Ding, W.; Bernan, V.; Richardson, A.; Ireland, C.; Greenstein, M.; Ellestad, G.; Carter, G. J. Am. Chem. Soc. 2001, 123, 5362-5363
2. For a comprehensive review of the lomaiviticins and kinamycins, see: Herzon, S. B.; Woo, C. M. Nat. Prod. Rep. 2012, 29, 87-118
3. Nicolaou, K. C.; Denton, R. M.; Lenzen, A.; Edmonds, D. J.; Li, A.; Milburn, R. R.; Harrison, S. T. Angew. Chem., Int. Ed. 2006, 45, 2076-2081
4. Krygowski, E. S.; Murphy-Benenato, K.; Shair, M. D. Angew. Chem., Int. Ed. 2008, 47, 1680-1684
5. Zhang, W.; Baranczak, A.; Sulikowski, G. A. Org. Lett. 2008, 10, 1939-1941
6. Nicolaou, K. C.; Nold, A. L.; Li, H. Angew. Chem., Int. Ed. 2009, 48, 5860-5863
7. Gholap, S. L.; Woo, C. M.; Ravikumar, P. C.; Herzon, S. B. Org. Lett. 2009, 11, 4322-4325
8. Lee, H. G.; Ahn, J. Y.; Lee, A. S.; Shair, M. D. Chem.-Eur. J. 2010, 16, 13058-13062
9. Morris, W. J.; Shair, M. D. Org. Lett. 2008, 11, 9-12
10. Morris, W. J.; Shair, M. D. Tetrahedron Lett. 2010, 51, 4310-4312
11. Herzon, S. B.; Lu, L.; Woo, C. M.; Gholap, S. L. J. Am. Chem. Soc. 2011, 133, 7260-7263
12. Herzon, S. B. Synlett 2011, 2105-2114
13. Barrett, A.; Graboski, G.; Russell, M. J. Org. Chem. 1985, 50, 2603-2605
14. Bordwell, F.; Bartmess, J. J. Org. Chem. 1978, 43, 3101-3107
15. Boivin, J.; Chauvet, C.; Zard, S. Z. Tetrahedron Lett. 1992, 33, 4913-4916
16. Ballini, R.; Bosica, G.; Fiorini, D.; Palmieri, A.; Petrini, M. Chem. Rev. 2005, 105, 933-971
17. Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 917-918
18. Ashwell, M.; Jackson, R. F. W.; Kirk, J. M. Tetrahedron 1990, 46, 7429-7442
19. Kim, S.; Park, J. H. Chem. Lett. 1988, 1323-1324
20. Ashwell, M.; Jackson, R. F. W. J. Chem. Soc., Chem. Commun. 1988, 282-283
21. Barrett, A. G. M.; Graboski, G. G.; Russell, M. A. J. Org. Chem. 1986, 51, 1012-1015
22. Miyashita, M.; Kumazawa, T.; Yoshikoshi, A. J. Chem. Soc., Chem. Commun. 1978, 362-363
23. Chuang, C.-P.; Wu, Y.-L.; Jiang, M.-C. Tetrahedron 1999, 55, 11229-11236
24. Chen, H.-L.; Lin, C.-Y.; Cheng, Y.-C.; Tsai, A.-I.; Chuang, C.-P. Synthesis 2005, 977-985
25. Tseng, C.-C.; Wu, Y.-L.; Chuang, C.-P. Tetrahedron 2002, 58, 7625-7633
26. Saraswathy, V. G.; Sankararaman, S. J. Org. Chem. 1995, 60, 5024-5028
27. Huot, R.; Brassard, P. Can. J. Chem. 1974, 52, 838-842