Enantioselective total synthesis of the indole alkaloid 16-episilicine

Chemical Communications

Volumn , Issue 20, 2009, Pages 2935-2937

  Amat, Mercedes ^a   Checa, Begoña ^a   Llor, Núria ^a   Molins, Elies ^b   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

16 EPISILICINE; BENZENE DERIVATIVE; BICYCLO COMPOUND; INDOLE ALKALOID; LACTAM DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALKYLATION; ARTICLE; CONJUGATION; ENANTIOSELECTIVITY; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 67449095775     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b904521j     Document Type: Article

References (35)

1. J. A. Joule, Indoles, The Monoterpenoid Indole Alkaloids, in The Chemistry of Heterocyclic Compounds, ed., J. E. Saxton, A. Weissberger, E. C. Taylor, Wiley, New York, vol. 25, part 4, 1983, pp. 232-239
2. B. Danieli and G. Palmisano, in The Alkaloids, ed., A. Brossi, Academic Press, Orlando, vol. 27, 1986, pp. 1-130
3. H. Zhang J.-M. Yue Helv. Chim. Acta 2005 88 2537
4. M. V. Kisakürek, A. J M. Leeuwenberg and M. Hesse, in Alkaloids: Chemical and Biological Perspectives, ed., S. W. Pelletier, Wiley, New York, 1983, ch. 5
5. J. Le Men W. I. Taylor Experientia 1965 21 508
6. F. Reis K. Bannai H.-P. Husson Tetrahedron Lett. 1976 1085
7. H.-P. Husson K. Bannai R. Freire B. Mompon F. A. M. Reis Tetrahedron 1978 34 1363
8. M.-L. Bennasar B. Vidal J. Bosch Chem. Commun. 1996 2755
9. M.-L. Bennasar B. Vidal R. Kumar A. Lázaro J. Bosch Eur. J. Org. Chem. 2000 3919
10. M. Zeches M. M. Debray G. Ledouble L. Le Men-Olivier J. Le Men Phytochemistry 1975 14 1122
11. P. Clivio B. Richard J.-M. Nuzillard M. Zèches-Hanrot Phytochemistry 1995 40 987
12. A.-M. Bui M.-M. Debray P. Boiteau P. Potier Phytochemistry 1977 16 703
13. D. Romo A. I. Meyers Tetrahedron 1991 47 9503
14. A. I. Meyers G. P. Brengel Chem. Commun. 1997 1
15. M. D. Groaning A. I. Meyers Tetrahedron 2000 56 9843
16. C. Escolano M. Amat J. Bosch Chem.-Eur. J. 2006 12 8198
17. M. Amat M. Pérez A. T. Minaglia B. Peretto J. Bosch Tetrahedron 2007 63 5839
18. M. Amat O. Lozano C. Escolano E. Molins J. Bosch J. Org. Chem. 2007 72 4431
19. M. Amat M. Pérez A. T. Minaglia J. Bosch J. Org. Chem. 2008 73 6920
20. I. Soteras O. Lozano C. Escolano M. Orozco M. Amat J. Bosch J. J. Luque J. Org. Chem. 2008 73 7756
21. M. Amat R. Griera R. Fabregat E. Molins J. Bosch Angew. Chem., Int. Ed. 2008 47 3348
22. M. Amat R. Fabregat R. Griera J. Bosch J. Org. Chem. 2009 74 1794
23. L. E. Overman A. J. Robichaud J. Am. Chem. Soc. 1989 111 300
24. M. Amat N. Llor J. Bosch X. Solans Tetrahedron 1997 53 719
25. J. Cossy O. Mirguet D. Gómez Pardo J.-R. Desmurs New J. Chem. 2003 27 475
26. A. Deiters M. Pettersson S. F. Martin J. Org. Chem. 2006 71 6547
27. M. Amat C. Escolano A. Gómez-Esqué O. Lozano N. Llor R. Griera E. Molins J. Bosch Tetrahedron: Asymmetry 2006 17 1581
28. P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon Press, Oxford, 1983, p. 221
29. P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon Press, Oxford, 1992, p. 25
30. D. W. M. Benzies P. Martinez-Fresneda R. A. Jones Synth. Commun. 1986 16 1799
31. Handbook of Metathesis, ed., R. H. Grubbs, Wiley-VCH, Weinheim, vol. 1-3, 2003
32. F.-X. Felpin J. Lebreton Eur. J. Org. Chem. 2003 3693
33. A. Deiters S. F. Martin Chem. Rev. 2004 104 2199
34. K. Yoshida J. Goto Y. Ban Chem. Pharm. Bull. 1987 35 4700
35. 3) of the isolated 16-episilicine