Synthetic Studies toward the Partial Ergot Alkaloid LY228729, a Potent 5HT1A Receptor Agonist

Journal of Organic Chemistry

Volumn 62, Issue 25, 1997, Pages 8640-8653

  Carr, M A ^a   Creviston, P E ^a   Hutchison, D R ^a   Kennedy, J H ^a   Khau, V V ^a   Kress, T J ^a   Leanna, M R ^a   Marshall, J D ^a   Martinelli, M J ^a   Peterson, B C ^a   Varie, D L ^a   Wepsiec, J P ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 DIPROPYLAMINO 1,3,4,5 TETRAHYDROBENZ[CD]INDOLE 6 CARBOXAMIDE; ERGOT ALKALOID; SEROTONIN AGONIST;

AROMATIZATION; ARTICLE; CONFORMATIONAL TRANSITION; CRYSTALLIZATION; DRUG SYNTHESIS; ENANTIOMER; EPOXIDATION; NEUROTRANSMITTER RELEASE; NONHUMAN; SIGNAL TRANSDUCTION;

EID: 0031466260     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971256z     Document Type: Article

References (36)

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33. Examples of intramolecular acylations of α-amino acid derivatives: (a) Melillo, D. G.; Larsen, R. D.; Mathre, D. J.; Shukis, W. F.; Wood, A. W.; Colleluori, J. R. J. Org. Chem. 1987, 52, 5143-50. (b) Buckley, T. F.; Rapoport, H. J. Org. Chem. 1983, 48, 4222-4232. McClure, D. E.; Lumma, P. K.; Arison, B. H.; Jones, J. H.; Baldwin, J. J. J. Org. Chem. 1983, 48, 2675-2679. McClure, D. E.; Arison, B. H.; Jones, J. H.; Baldwin, J. J. J. Org. Chem. 1981, 46, 2431-2433.
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36. 2 was much slower than the cyclization of the acid chloride. Less than 5% ketone 30 was formed after 7 h, whereas 80% of the acid chloride 26c was converted to 30 in the same time.