Expanding the scope of Mn(OAc)3-mediated cyclizations: Synthesis of the tetracyclic core of tronocarpine

Organic Letters

Volumn 8, Issue 20, 2006, Pages 4561-4564

  Magolan, Jakob ^a   Kerr, Michael A ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AZEPINE DERIVATIVE; INDOLE ALKALOID; MANGANESE DERIVATIVE; TRONOCARPINE;

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

AZEPINES; CYCLIZATION; INDOLE ALKALOIDS; MANGANESE COMPOUNDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 33750039373     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061698+     Document Type: Article

References (20)

1. (a) Gul, W.; Hamann, M. T. Life Sci. 2005, 78, 442.
2. (b) Cordell, G. G. A. The Alkaloids: Chemistry and Biology; Elsevier Science: San Diego, 2003; Vol. 60.
3. (a) Tronocarpine: Kam, T.-S.; Sim, K.-M.; Lim, T.-M. Tetrahedron Lett. 2000, 41, 2733.
4. (b) Mersicarpine: Kam, T.-S.; Subramaniam, G.; Lim, K.-H.; Choo, Y.-M. Tetrahedron Lett. 2004, 45, 5995.
5. (c) Rhazinal: Kam, T.-S.; Tee, Y.-M.; Subramaniam, G. Nat. Prod. Lett. 1998, 12, 307.
6. Banwell, M. G.; Edwards, A. J.; Jolliffe, K. A.; Smith, J. A.; Hamel, E.; Verdier-Pinard, P. Org. Biomol. Chem. 2003, 1, 296
7. 3 chemistry, see: (a) Snider, B. B. Chem. Rev. 1996, 96, 339.
8. (b) Snider, Barry B. Manganese(III)-based oxidative free-radical cyclizations. In Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bolm, C., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2004; Vol. 1, pp 483-490.
9. (a) Tsai, A.-I.; Lin, C.-H.; Chuang, C. P. Heterocycles 2005, 65, 2381.
10. (b) Chuang, C. P.; Wang, S. F. Tetrahedron Lett. 1994, 55, 1283.
11. (c) Artis D. R.; Cho I.-S.; Muchowski, J. M. Can. J. Chem. 1992, 70, 1838.
12. (a) Fristad, W. E.; Peterson, J. R. J. Org. Chem. 1985, 50, 10.
13. (b) Fristad, W. E.; Hershberger, S. S. J. Org. Chem. 1985, 50, 1026.
14. (c) Fristad, W. E.; Peterson, J. R.; Ernst, A. B. J. Org. Chem. 1985, 50, 3143.
15. (d) Yang, F. Z.; Trost, M. K.; Fristad, W. E. Tetrahedron Lett. 1987, 28, 1493.
16. Compound 30 was prepared from the corresponding carboxylic acid: Prabhu, K. R.; Pillarsetty, N.; Gali, H.; Katti, K. V. J. Am. Chem. Soc. 2000, 122, 1554.
17. Dehaen, W.; Hassner, A. J. Org. Chem. 1991, 56, 896.
18. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353.
19. Ketcha, D. M. Tetrahedron Lett. 1988, 29, 2151.
20. Compound 41 has been reported in the literature (Mahboobi, v. S.; Burgemeister, T.; Kastner, F. Arch. Pharm. Weinheim, Ger. 1995, 328, 29). For a comparison of spectral data, see the Supporting Information.