An asymmetric aminohydroxylation approach to the azepine core of (-)-balanol

Organic Letters

Volumn 2, Issue 17, 2000, Pages 2571-2573

  Masse, Craig E ^a   Morgan, Adam J ^a   Panek, James S ^a  

^a BOSTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZEPINE DERIVATIVE; BALANOL; ENZYME INHIBITOR; HYDROXYBENZOIC ACID DERIVATIVE; PROTEIN KINASE C;

AMINATION; ARTICLE; DRUG ANTAGONISM; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

AMINATION; AZEPINES; ENZYME INHIBITORS; HYDROXYBENZOIC ACIDS; HYDROXYLATION; MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN KINASE C;

EID: 0034710481     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0061034     Document Type: Article

References (23)

1. Kulanthaivel, P.; Hallock, Y. F.; Boros, C.; Hamilton, S. M.; Janzen, W. P.; Ballas, L. M.; Loomis, C. R.; Jiang, J. B.; Katz, B.; Steiner, J. R.; Clardy, J. J. Am. Chem. Soc. 1993, 115, 6452-6453.
2. Ohshima, S.; Yanagisawa, M. Katoh, A.; Fujii, T.; Sano, T.; Matsukama, S.; Furumai, T.; Fujiu, M.; Watanabe, K.; Yokose, K.; Arisawa, M.; Okuda, T. J. Antibiot. 1994, 47, 639-641.
3. Nishizuka, Y. Science 1992, 258, 607-614.
4. (b) Nishizuka, Y. Nature 1988, 334, 661-665.
5. Three-dimensional modeling was carried out with Chem 3D Pro using MM2 minimization techniques.
6. Boros, C.; Hamilton, S. M.; Katz, B.; Kulanthaivel, P. J. Antibiot. 1994, 47, 1010-1016.
7. Miyabe, H.; Torieda, M.; Inoue, K.; Tajiri, K.; Kiguchi, T.; Naito, T. J. Org. Chem. 1998, 63, 4397-4407.
8. Adams, C. P.; Fairway, S. M.; Hardy, C. J.; Hibbs, D. E.; Hursthouse, M. B.; Morley, A. D.; Sharp, B. W.; Vicker, N.; Warner, I. J. Chem Soc., Perkin Trans. 1 1995, 2335-2362.
9. Tanner, D.; Almario, A. Högberg, T. Tetrahedron 1995, 51, 6061-6070.
10. Nicolaou, K. C.; Bunnage, M. E.; Koide, K. J. Am. Chem. Soc. 1994, 116, 8402-8403.
11. Lampe, J. W.; Hughes, P. F.; Biggers, C. K.; Smith, S. H.; Hu, H. J. Org. Chem. 1996, 61, 4572-4581.
12. (a) Fürstner, A.; Thiel, O. R. J. Org. Chem. 2000, 65, 1738-1742.
13. (b) Cook, G. R.; Shanker, P. S.; Peterson, S. L. Org. Lett. 1999, 1, 615-617.
14. (c) Morie, T.; Kato, S. Heterocycles 1998, 48, 427-431.
15. (d) Wu, M. H.; Jacobsen, E. N. Tetrahedron Lett. 1997, 38, 1693-1696.
16. (e) Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron 1997, 53, 17177-17182.
17. (f) Tuch, A.; Saniere, M.; Le Merrer, Y.; Depezay, J.-C. Tetrahedron: Asymmetry 1996, 7, 2901-2905.
18. (g) Müler, A.; Takyar, D. K.; Witt, S.; König, W. A. Liebigs Ann. Chem. 1993, 651-655.
19. (a) Morgan, A. J.; Masse, C. E.; Panek, J. S. Org. Lett. 1999, 1, 1949-1952.
20. (b) Panek, J. S.; Masse, C. E. Angew. Chem., Int. Ed. 1999, 38, 1093-1095.
21. Determined by Mosher Analysis: see Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-513 and Supporting Information.
22. Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2813-2816.
23. Belyaev, A. A. U.S. Patent 1708812-A1, January 30, 1994.