Synthesis of the cores of hypocrellin and shiraiachrome: diastereoselective 1,8-diketone aldol cyclization

Journal of Organic Chemistry

Volumn 75, Issue 1, 2010, Pages 69-73

  O'Brien, Erin M ^a   Li, Jingxian ^a   Carroll, Patrick J ^a   Kozlowski, Marisa C ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL REACTIONS; CHEMICAL EQUATIONS; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE; DIKETONES; HIGH SELECTIVITY; NATURAL PRODUCTS; NINE-MEMBERED RINGS; SEVEN-MEMBERED RINGS;

STEREOSELECTIVITY;

KETONES;

1,8 DIKETONE; AMINE; AZIDE; DIKETONE; HYPOCRELLIN; NATURAL PRODUCT; QUINONE DERIVATIVE; SHIRAIACHROME; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; FEASIBILITY STUDY; HUMAN; STEREOCHEMISTRY;

ALDEHYDES; CATALYSIS; CYCLIZATION; KETONES; MOLECULAR STRUCTURE; PERYLENE; QUINONES; STEREOISOMERISM;

EID: 73449097131     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9018914     Document Type: Article

References (33)

1. For reviews see: (a) Weiss, U.; Merlini, L.; Nasini, G. Prog. Chem. Org. Nat. Prod. 1987, 52, 1-71.
2. (b) Bringmann, G.; Günther, C.; Ochse, M.; Schupp, O.; Tasler, S. Prog. Chem. Org. Nat. Prod. 2001, 82, 1-249.
3. Chen, W. S.; Chen, Y. T.; Wang, X. Y.; Friedrichs, E.; Puff, H.; Breitmaier, E. Liebigs Ann. Chem. 1981, 1880-1885.
4. (a) Lown, J. W. Can. J. Chem. 1997, 75, 99-119.
5. (b) Towers, G. H. N.; Page, J. E.; Hudson, J. B. Curr. Org. Chem. 1997, 1, 395-414.
6. Mazzini, S.; Merlini, L.; Mondelli, R.; Scagloni, L. J. Chem. Soc., Perkin Trans. 2 2001, 409-416.
7. (a) Ali, S. M.; Chee, S. K.; Yuen, G. Y.; Olivo, M. J. Photochem. Photobiol. B 2001, 65, 59-73.
8. (b) Ali, S. M.; Olivo, M.; Yuen, G. Y.; Chee, S. K. Int. J. Oncol. 2001, 19, 633-643.
9. (c) Zhang, J.; Cao, E.-H.; Li, J.-F.; Zhang, T.-C.; Ma, W.-J. J. Photochem. Photobiol. B 1998, 43, 106-111.
10. (d) Ma, L.; Tai, H.; Li, C.; Zhang, Y.; Wang, Z.-H.; Ji, W.-Z. World J. Gastroenterol. 2003, 9, 485-490.
11. (a) Hudson, J. B.; Imperial, V.; Haugland, R. P.; Diwu, Z. Photochem. Photobiol. 1997, 65, 352-354.
12. (b) Hirayama, J.; Ikebuchi, K.; Abe, H.; Kwon, K.-W.; Ohnishi, Y.; Horiuchi, M.; Shinagawa, M.; Ikuta, K.; Kamo, N.; Sekiguchi, S. Photochem. Photobiol. 1997, 66, 697-700.
13. Leveugle, B. U. S. Patent 2001-264677, 2002.
14. Selected examples: (a) Baciagaluppo, J. A.; Colombo, M. I.; Cravero, R. M.; González-Sierra, M.; Preite, M. D.; Zinczuk, J.; Rúveda, E. A. Tetrahedron: Asymmetry 1994, 5, 1877-1880.
15. (b) Jung, M. E.; Johnson, T. W. J. Am. Chem. Soc. 1997, 119, 12412-12413.
16. (c) Kaji, Y.; Koami, T.; Nakamura, A.; Fujimoto, Y. Chem. Pharm. Bull. 2000, 48, 1480-1483.
17. For selected examples, see: (a) Miyahara, Y. J. Org. Chem. 2006, 71, 6516-6521.
18. (b) Davies, S.; Sheppard, R. L.; Smith, A. D.; Thomson, J. E. Chem. Commun. 2005, 3802-3804.
19. (c) Piers, E.; Skupinska, K. A.; Wallace, D. J. Synlett 1999, 12, 1867-1870.
20. (d) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420.
21. (e) Shizuri, Y.; Ohtsuka, J.; Kosemura, S.; Terada, Y.; Yamamura, S. Tetrahedron Lett. 1984, 25, 5547-5550.
22. Baik, T. G.; Luis, A. L.; Wang, L. C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112-5113.
23. Dyker, G.; Thoene, A. J. Prakt. Chem. 1999, 341, 138-141.
24. Carroll, A. R.; Read, R. W.; Taylor, W. C. Aust. J. Chem. 1994, 47, 1579-1589.
25. See the Supporting Information.
26. (a) Gaudemer, M.; Bellassoued, M. Tetrahedron Lett. 1989, 30, 2779-2782.
27. (b) Masamune, S.; Ellingboe, J.; Choy, W. J. Am. Chem. Soc. 1982, 104, 5526-5528.
28. (a) MacroModel 6.5: Still, W. C. Columbia University.
29. (b) Mohamdi, F.; Richards, N. G.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
30. (a) O'Brien, E. M.; Morgan, B. J.; Kozlowski, M. C. Angew. Chem., Int. Ed. 2008, 47, 6877-6880.
31. (b) See also the next manuscript in this series.
32. Collum, D. B.; Godenschwager, P. F. J. Am. Chem. Soc. 2008, 130, 8726-8732.
33. Collum, D. B.; Hall, P. L.; Gilchrist, J. H. J. Am. Chem. Soc. 1991, 113, 9571-9574.