Solid-phase synthesis of 2,3,5-Trisubstituted indoles

Organic Letters

Volumn 3, Issue 24, 2001, Pages 3827-3830

  Wu, Tom Y H ^a   Ding, Sheng ^a   Gray, Nathanael S ^b   Schultz, Peter G ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b GENOMICS INSTITUTE OF THE NOVARTIS RESEARCH FOUNDATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002623305     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016525t     Document Type: Article

References (21)

1. (a) Kerber, V. A.; Gregianini, T. S.; Paranhos, J. T.; Schwambach, J.; Farias, F.; Fett, J. P.; Fett-Neto, A. G.; Zuanazzi, J. A. S.; Quirion, J. C.; Elizabetsky, E.; Henriques, A. T. J. Nat. Prod. 2001, 64, 677-679.
2. (b) Gerasimenko, I.; Sheludko, Y.; Stockigt, J. J. Nat. Prod. 2001, 64, 114-116.
3. For recent reviews of indole chemistry, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045-1075.
4. (b) Li, J. J.; Gribble, G. W. In Tetrahedron Organic Chemistry Series: Palladium in Heterocyclic Chemistry; Baldwin, J. E., Williams, F. R. S., Williams, R. M., Eds.; Elsevier Science: Oxford, 2000; Vol. 20, pp 73-182.
5. For recent reviews of combinatorial chemistry, see (a) Dolle, R. E.; Nelson, K. H., Jr. J. Comb. Chem. 1999, 1, 235-282.
6. (b) Dolle, R. E. J. Comb. Chem. 2000, 2, 383-433 and references therein.
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8. (b) Fancelli, D.; Fagnola, M. C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311-2314.
9. (c) Zhang, H.-C.; Brumfield, K. K.; Maryanoff, B. E. Tetrahedron Lett. 1997, 38, 2439-2442.
10. (a) Zhang, H.-C.; Ye, H.; Moretto, A. F., Brumfield, K. K.; Maryanoff, B. E. Org. Lett. 2000, 2, 89-92.
11. (b) Smith, A. L.; Stevenson, G. I.; Swain, C. J.; Castro, J. L. Tetrahedron Lett. 1998, 39, 8317-8320.
12. (c) Smith, A. L.; Stevenson, G. I.; Lewis, S.; Patel, S.; Castro, J. L. Bioorg. Med. Chem. Lett. 2000, 10, 2693-2696.
13. 3 = phenyl (introduced using benzoyl chloride and phenylboronic acid as shown in Scheme 1). RP-LCMS shows >95% purity based on UV absorption at 255 nm.
14. Okauchi, T.; Itonaga, M.; Minami, T.; Owa, T.; Kitoh, K.; Yoshino, H. Org. Lett. 2000, 2, 1485-1487.
15. Ketcha, D. M.; Gribble, G. W. J. Org. Chem. 1985, 50, 5451-5457.
16. 3 = phenyl (introduced using phenylacetylene and phenylboronic acid as shown in Scheme 1). RP-LCMS shows >95% purity based on UV absorption at 255 nm.
17. 2 = phenyl (introduced using phenylacetylene and benzoyl chloride as shown in Scheme 1). RP-LCMS shows >95% purity based on UV absorption at 255 nm.
18. Johnson, C. N.; Stemp, G.; Anand, N.; Stephen, S. C.; Gallagher, T. Synlett 1998, 1025-1027.
19. Schoepfer, J.; Merklen, P.; Scheffel, G. Unpublished results.
20. Reaction with 3,4-dimethoxyphenylboronic acid after 1 day still showed ∼30% unreacted starting material plus ∼70% desired product. Elevated temperature and/or prolonged reaction time did not seem to increase the product to starting material ratio.
21. 2 = phenyl (introduced using phenylacetylene and benzoyl chloride as shown in Scheme 1). RP-LCMS shows >95% purity based on UV absorption at 255 nm.