Convergent and short-step syntheses of dl-Cypridina luciferin and its analogues based on Pd-mediated cross couplings

Tetrahedron Letters

Volumn 41, Issue 13, 2000, Pages 2185-2188

  Nakamura, Hideshi ^a   Aizawa, Mihoko ^b   Takeuchi, Daisuke ^b   Murai, Akio ^b   Shimoura, Osamu ^c  

^a Dept Appl Molec Biosci Grad S   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

^c MARINE BIOLOGICAL LABORATORY   (United States)

Author keywords

Benzofurans; Benzothiophenes; Bioluminescence; Indoles

Indexed keywords

BENZOFURAN DERIVATIVE; BENZOTHIOPHENE DERIVATIVE; LUCIFERASE; LUCIFERIN; PALLADIUM; PYRAZINE DERIVATIVE;

ARTICLE; BIOLUMINESCENCE; CHEMICAL ANALYSIS; CHEMOLUMINESCENCE; MOLECULAR RECOGNITION; SYNTHESIS;

EID: 0034719836     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00131-3     Document Type: Article

References (22)

1. Shimomura, O.; Johnson, F. H.; Masugi, T. Science 1969, 164, 1299-1300.
2. Kishi, Y.; Goto, T.; Inoue, S.; Sugiura, S.; Kishimoto, H. Tetrahedron Lett. 1966, 3445-3450.
3. Karpetsky, T. P.; White, E. H. J. Am. Chem. Soc. 1971, 93, 2333-2334. Idem, Tetrahedron 1973, 29, 3761-3773.
4. Karpetsky, T. P.; White, E. H. J. Am. Chem. Soc. 1971, 93, 2333-2334. Idem, Tetrahedron 1973, 29, 3761-3773.
5. Goto, T. Pure Appl. Chem. 1968, 17, 421-441.
6. (a) Nakamura, H.; Takeuchi, D.; Murai, A. Synlett 1995, 1227-1228.
7. (b) Nakamura, H.; Aizawa, M.; Murai, A. Synlett 1996, 1015-1017.
8. (c) Nakamura, H.; Wu, C.; Murai, A.; Inouye, S.; Shimomura, O. Tetrahedron Lett. 1997, 38, 6405-6406.
9. Sato, N. J. Heterocycl. Chem. 1982, 673-674.
10. Sonogashira, K. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, Chapter 2.3, pp. 521-529.
11. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
12. (b) It could not be achieved by Stille coupling with 1-t-butyldimethylsilyl-3-tributylstannylindole but might be possible with 1-tosyl-3-trimethylstannylindole: Cianttini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1994, 35, 2405-2408.
13. Zheng, Q.; Yang, Y.; Martin, A. R. Heterocycles 1994, 37, 1761-1772.
14. Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. J. Org. Chem. 1992, 57, 2497-2502.
15. The reaction conditions were not optimized yet at small scale reactions, and the condensation with a ketoaldehyde was reported as good (80%) at a several hundred mg scale. Sugiura, S.; Inoue, S.; Goto, T. Yakugaku Zasshi 1970, 90, 707-710.
16. max 430 nm (ε 10400).
17. For a recent review, see: Wilson, T.; Hastings, J. W. Annu. Rev. Cell Dev. Biol. 1998, 14, 197-230.
18. Similar findings in an indolactam-protein kinase C interaction were reported by: Kozikowski, A. P.; Ma, D.; Du, L.; Lewin, N. E.; Blumberg, P. M. J. Am. Chem. Soc. 1995, 117, 6666-6672.
19. Kubota, H. Y.; Yoshimoto, Y.; Yoneda, M.; Hiramoto, Y. Dev. Biol. 1987 19, 129-136.
20. (a) Inouye, S.; Ohmiya, Y.; Toya, Y.; Tsuji F. I. Proc. Natl. Acad. Sci. USA 1992, 89, 9584-9587.
21. (b) Thompson, E. M.; Adenot, P.; Tsuji, F. I.; Renard, J. P. Proc. Natl. Acad. Sci. USA 1995, 92, 1317-1321.
22. (c) Miesenböck, G.; Rothman, J. E. Proc. Natl. Acad. Sci. USA 1997, 94, 3402-3407.