A flexible, convergent approach to polycyclic indole structures: Formal synthesis of (±)-mersicarpine

Organic Letters

Volumn 11, Issue 13, 2009, Pages 2800-2803

  Blechy, Auréllen ^a   Zard, Samir Z ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOID; INDOLE DERIVATIVE; MERSICARPINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; INDOLE ALKALOIDS; INDOLES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 67649460749     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900996k     Document Type: Article

References (27)

1. Kam, T. S.; Subramaniam, G.; Lim, K. H.; Choo, Y. M. Tetrahedron Lett. 2004, 45, 5995.
2. Magolan, J.; Carson, C. A.; Kerr, M. A. Org. Lett. 2008, 10, 1437.
3. Seguin, S. Ph.D. Dissertation, Ecole Polytechnique, Palaiseau, 1999.
4. (a) Reyes-Gutiérrez, P. E.; Torres-Ochoa, R. O.; Martínez, R.; Miranda, L. D. Org. Biomol. Chem. 2009, 7, 1388.
5. (b) Guerrero, M. A.; Miranda, L. D. Tetrahedron Lett. 2006, 47, 25.17.
6. (c) Osornio, Y. M.; CruzAlmanza, R.; Jiménez-Montaño, V.; Miranda, L. D. Chem. Commun. 2003, 2316.
7. (d) Magolan, J.; Kerr, M. Org. Lett. 2006, 8, 4561.
8. (e) Gross, S.; Reissig, H. U. Org. Lett. 2003, 5, 4305.
9. For reviews of the xanthate transfer chemistry, see: (a) Zard, S. Z. Angew. Chem., Int. Ed. Engl. 1997, 36, 672.
10. (b) Zard, S. Z. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH; Weinheim 2001, Vol. 1, p 90.
11. (c) Quiclet-Sire, B.; Zard, S. Z. Chem.-Eur. J. 2006, 12, 6002.
12. (d) Quiclet-Sire, B.; Zard, S. Z. Top. Curr. Chem. 2006, 264, 201.
13. (e) Zard, S. Z. Org. Biomol. Chem. 2007, 5, 205.
14. (a) Coste, A.; Toumi, M.; Wright, K.; Razafimahaléo, V.; Couty, F.; Marrot, J.; Evano, G. Org. Lett. 2008, 10, 3841.
15. (b) Toumi, M.; Couty, F.; Marrot, J.; Evano, G. Org. Lett. 2008, 10, 5027.
16. (a) Janosik, T.; Shirani, H.; Wahlström, N.; Malky, I.; Stensland, B.; Bergman, J. Tetrahedron 2006, 62, 1699.
17. (b) Ludwig, J.; Lehr, M. Synth. Commun. 2004, 34, 3691.
18. (c) Battaglia, S.; Boldrini, E.; Da Settimo, F.; Dondio, G.; La Motta, C.; Marini, A. M.; Primofiore, G. Eur. J. Med. Chem. 1999, 34, 93.
19. (d) Stanovnik, B.; Tišler, M.; Carlock, J. T. Synthesis 1976, 754.
20. The addition of radicals to aromatic rings is known to be reversible. See:
21. (a) Citterio, A.; Minisci, F.; Porta, O.; Sesana, G. J. Am. Chem. Soc. 1977, 99, 7960.
22. (b) Griller, D.; Marriott, P. R.; Nonhebel, D. C.; Perkins, M. J.; Wong, P. C. J. Am. Chem. Soc. 1981, 103, 7761. The reverse reaction, i.e., the fragmentation of the cyclohexadienyl radicals, has been elegantly applied in synthesis.
23. For a review, see: (c) Walton, J. C.; Studer, A. Acc. Chem. Res. 2005, 38, 794.
24. For the preparation of the corresponding methyl ester, see: Časar, Z.; Bevk, D.; Svete, J.; Stanovnik, B. Tetrahedron 2005, 61, 7508.
25. (a) McCaffery, E. L.; Shalaby, S. W. J. Organomet. Chem. 1967, 8, 17.
26. (b) Exon, C.; Gallagher, T.; Magnus, P. J. Am. Chem. Soc. 1983, 105, 4739.
27. It may be interesting to replace the fert-butoxycarbonyl group in 10 with a carboxamide derived from a non-racemic chiral amine, as this may allow control of the absolute stereochemistry in the cyclization step.