Swern oxidation of tryptamine derivatives

Tetrahedron Letters

Volumn 40, Issue 24, 1999, Pages 4593-4596

  Bailey, Patrick D ^a   Cochrane, Philip J ^a   Irvine, Frances ^a   Morgan, Keith M ^a   Pearson, David P J ^b   Veal, Kenneth T ^c  

^a HERIOT WATT UNIVERSITY   (United Kingdom)

^b JEALOTT S HILL RESEARCH STATION   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Indoles; Oxidation; Rearrangements; Swern

Indexed keywords

INDOLE DERIVATIVE; TRYPTAMINE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; CYCLIZATION; OXIDATION; PROTON TRANSPORT;

EID: 0033546353     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00692-9     Document Type: Article

References (25)

1. [1] a) Isolation of 1a: Yamazaki M, Fujimoto H, Okuyama E, Ohta Y. Proc. Jpn. Assoc. Mycotoxicol. 1980, 10, 27; isolation of1b: Ondeyka JG, Goegelmao RT, Schaeffer JM, Kelemen, Zitano L. J. Antibiotics 1990, 43, 1375.
2. [1] a) Isolation of 1a: Yamazaki M, Fujimoto H, Okuyama E, Ohta Y. Proc. Jpn. Assoc. Mycotoxicol. 1980, 10, 27; isolation of 1b: Ondeyka JG, Goegelmao RT, Schaeffer JM, Kelemen, Zitano L. J. Antibiotics 1990, 43, 1375.
3. b) Structure of 1a: Yamazaki M, Okuyama E, Kobayashi M, Inoue H. Tetrahedron Lett. 1981, 22, 135; structure of 1b: Liesch JM, Wichmann CF. J. Antibiotics1990, 43, 1380.
4. b) Structure of 1a: YamazakiM, Okuyama E, Kobayashi M, Inoue H. Tetrahedron Lett. 1981, 22, 135; structure of 1b: Liesch JM, Wichmann CF. J. Antibiotics 1990, 43, 1380.
5. c) Synthesis of 1b: Cushing TD, Sanz-Cervera JF, Williams RM. 1993, 115, 9323.
6. [2] a) Isolation: Birch AJ, Wright JJ. Tetrahedron 1970, 26, 2329.
7. b) Structure: Birch AJ, Russell RA. Tetrahedron 1972, 28, 2999.
8. c) Synthesis: Kametani T, Kanaya N, Ihara M. J. Chem. Soc., Perkin Trans. 1 1981, 959.
9. [3] a) Isolation: Cui C-B, Kakeya H, Okada G, Onose R, Osada H. J. Antibiotics 1996, 49, 527.
10. b) Structure: Cui C-B, Kakeya H, Osada H. J. Antibiotics 1996, 49, 534.
11. c) Syntheses: Depew KM, Danishefsky SJ, Rosen N, Sepp-Lorenzino L. J. Am. Chem. Soc. 1996, 118, 12463; Gan T, Cook JM. Tetrahedron Lett. 1997, 38, 1301.
12. c) Syntheses: Depew KM, Danishefsky SJ, Rosen N, Sepp-Lorenzino L. J. Am. Chem. Soc.1996, 118, 12463; Gan T, Cook JM. Tetrahedron Lett. 1997, 38, 1301.
13. [4] Isolation and structure: Hayashi H, Takiuchi K, Murao S. Arai M. Agric. Biol. Chem. 1989, 53, 461.
14. [5] Schkeryantz JM, Woo JCG, Danishefsky SJ. J. Am. Chem. Soc. 1995, 117, 7025.
15. [6] Cushing TD, Sanz-Cervera JF, Williams RM. J. Am. Chem. Soc. 1993, 115, 9323.
16. [7] Szabó-Pusztay K, Szabó L. Synthesis 1979, 276.
17. [8] Ohno M, Spande TF, Witkop B. J. Am. Chem. Soc. 1970, 92, 343.
18. [9] Manucuso AJ, Swern D. Synthesis 1981, 165.
19. [10] Tidwell TT. Synthesis 1990, 857.
20. [11] Omura K, Sharma AK, Swern D. J. Org. Chem. 1976, 41, 957.
21. [12] Manucuso AJ, Huang S-L, Swern D. J. Org. Chem. 1978, 43, 2480.
22. [13] In Spectroscopic Methods in Organic Chemistry (4th edition), Williams DH and Fleming I, Mcgraw-Hill, 1987, p131.
23. [14] Sharma AK, Ku T, Dawson AD, Swern D. J. Org. Chem. 1975, 40, 2758.
24. [15] Hauser CR, Kantor SW, Brasen WR. J. Am. Chem. Soc. 1953, 75, 2660.
25. [16] Somei M, Kawasaki T, Fukui Y, Yamada F, Kobayashi T, Aoyama H, Shinmyo D. Heterocycles 1992, 34, 1877.