Use of azalactones in a 'Pictet-Spengler-like' reaction. Stereoselective synthesis of 1,3,4-substituted tetrahydro-β-carbolines

Tetrahedron Letters

Volumn 37, Issue 32, 1996, Pages 5813-5816

  Ezquerra, Jesús ^a   Lamas, Carlos ^a   Pastor, Alfredo ^b   Alvarez, Pilar ^b   Vaquero, Juan José ^b   Prowse, Will G ^c  

^a CSIC   (Spain)

^b UNIVERSITY OF ALCALÁ   (Spain)

^c ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TRYPTOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030570892     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01233-6     Document Type: Article

References (18)

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4. 4. Audia, J. A.; Droste, J. J.; Nissen, J. S.; Murdoch, G. R.; Evard, D. A. J. Org. Chem. 1996, (In press)
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10. (b) Bailey, P. D.; Hollinshead, S. P.; McLay, N. R.; Morgan, K.; Palmer, S. J.; Prince, S. N.; Reynolds, C. D.; Wood, S. D. J. Chem. Soc. Perkin Trans 1, 1993, 431-439.
11. (c) Bailey, P. D.; McLay, N. R. J. Chem. Soc. Perkin Trans 1, 1993, 441-449.
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15. 12. Plöchl, J.; Ber, 1883, 16, 2815-2825
16. 13. General Procedure for the synthesis of tetrahydro-β-carboline hydrochlorides 3: A suspension of the tryptamines hydrochloride 4 (1 mmol) and the correponding 4-alkylidene-2-methyloxazolin-5-one (1.2 mmol) was refluxed under Ar atmosphere for 72 h. After this time the reaction mixture was allowed to reach room temperature and tetrahydro-β-carboline hydrochlorides isolated by filtration. Finally, the crude solid was purified by flash chromatography using dichloromethane/methanol (9:1) as eluent.
17. 14. The C-1 trans THBC was not detected in the reaction mother liquor after isolation of the cis products.
18. 15. Ghosh, A.; Wang, W.; Freeman, J. P.; Althaus, J. S.; VonVolgtlander, P. F.; Scahill, T. A.; Mizsak, S. A.; Szmuszkovicz, J. Tetrahedron 1991, 47, 8653-8662.