Synthesis of indoles isolated from Tricholoma species

Journal of Organic Chemistry

Volumn 64, Issue 26, 1999, Pages 9731-9734

  Söderberg, Björn C ^a   Chisnell, Angela C ^a   O'Neil, Shannon N ^a   Shriver, James A ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ALKALOID; CARBON MONOXIDE; INDOLE DERIVATIVE; NITROBENZENE DERIVATIVE; PALLADIUM; TIN DERIVATIVE; TRIPHENYLPHOSPHINE;

ARTICLE; BASIDIOMYCETES; BROMINATION; CATALYSIS; CHEMICAL REACTION; CIS TRANS ISOMERISM; EXTRACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037957571     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991208+     Document Type: Article

References (26)

1. (a) Söderberg, B. C.; Rector, S. R.; O'Neil, S. N. Tetrahedron Lett. 1999, 40, 3657.
2. (b) Söderberg, B. C.; Shriver, J. A. J. Org. Chem. 1997, 62, 5838.
3. See also (a) Akazome, M.; Kondo, T.; Watanabe, Y. J. Org. Chem. 1994, 59, 3375.
4. (b) Tolari, S.; Cenini, S, Crotti, C.; Gianella, E. J. Mol. Catal. 1994, 87, 2811.
5. (c) Tolari, S.; Cenini, S, Crotti, C.; Gianella, E. J. Mol. Catal. 1994, 87, 203.
6. (d) Crotti, C.; Cenini, R.; Todeschini, R.; Tollari, S. J. Chem. Soc., Faraday Trans. 1991, 2811.
7. (e) Crotti, C.; Cenini, S.; Rindone, B.; Tollari, S.; Demartin, F. J. Chem. Soc., Chem. Commun. 1986, 784.
8. Garlaschelli, L.; Pang, Z.; Sterner, O.; Vidari, G. Tetrahedron 1994, 50, 3541.
9. Stachel, S. J.; Nilges, M.; Van Vranken, D. L. J. Org. Chem. 1997, 62, 4756.
10. Krolski, M. E.; Renaldo, A. F.; Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1988, 53, 1170.
11. For an excellent review, see: Farina, V.; Krishnamurthy, V.; Scott, V. J. In Organic Reactions; John Wiley & Sons: New York, 1997; Vol. 50, pp 1-652.
12. (a) Reference 4.
13. (b) Bard, R. R.; Bunnett, J. F. J. Org. Chem. 1980, 45, 1546.
14. (c) MacDonald, G.; Proctor, G. R. J. Chem. Soc., Chem. Commun. 1975, 1446.
15. (d) Gassman, P. G.; van Bergen, T. J.; Gilbert, D. P.; Cue, B. W., Jr. J. Am. Chem. Soc. 1974, 96, 6, 5495.
16. For a related reduction, see Kozikowski, A. P.; Ishida, H.; Chen, Y.-Y. J. Org. Chem. 1980, 45, 3350.
17. For similar hydrolytic cleavages of ylides, see Maercher, A. Org. React. 1965, 14, 291. And references therein: (a) Wittig, G.; Geissler, G. Justus Lieb. Ann. Chem. 1953, 580, 44. (b) Fenton, G. W.; Ingold, C. K. J. Chem. Soc. 1929, 2342.
18. For similar hydrolytic cleavages of ylides, see Maercher, A. Org. React. 1965, 14, 291. And references therein: (a) Wittig, G.; Geissler, G. Justus Lieb. Ann. Chem. 1953, 580, 44. (b) Fenton, G. W.; Ingold, C. K. J. Chem. Soc. 1929, 2342.
19. For similar hydrolytic cleavages of ylides, see Maercher, A. Org. React. 1965, 14, 291. And references therein: (a) Wittig, G.; Geissler, G. Justus Lieb. Ann. Chem. 1953, 580, 44. (b) Fenton, G. W.; Ingold, C. K. J. Chem. Soc. 1929, 2342.
20. Plummer, E. L. U.S. Patent. US 4,329,518, 1982; Chem. Abstr. 1982, 97, 91961f.
21. Plummer, E. L. U.S. Patent. US 4,329,518, 1982; Chem. Abstr. 1982, 97, 91961f.
22. 1H NMR δ 8.27 (dd, J = 7.9 and 1.6 Hz, 1H), 7.68 (dd, J = 7.9 and 1.6 Hz, 1H), 7.58 (t, J = 7 9 Hz, 1H), 7.15 (s, 1H).
23. Seyferth, D.; Vaugan, L. G. J. Organomet. Chem. 1963, 1, 138.
24. 13C NMR resonances are based on the intensity of the resonances and are tentative.
25. Prepared from 2-bromo-3-nitrobenzoic acid (Organic Syntheses; Wiley: New York, 1941; Coll. Vol. 1, p 125) according to ref 6.
26. Horning, D. E.; Lacasse, G.; Muchowski, J. M. Can. J. Chem. 1971, 49, 2797.