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Volumn 52, Issue 31, 2011, Pages 4042-4044

Concise syntheses of 5,6-dibromotryptamine and 5,6-dibromo-N,N- dimethyltryptamine en route to the antibiotic alternatamide D

Author keywords

5,6 Dibromoindole; Alkaloid; Alternatamide; Natural product; Tryptamine

Indexed keywords

5,6 DIBROMO N,N DIMETHYLTRYPTAMINE; 5,6 DIBROMOTRYPTAMINE; ALTERNATAMIDE D; ANTIBIOTIC AGENT; INDOLE DERIVATIVE; NATURAL PRODUCT; TRYPTAMINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79959873863     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.05.126     Document Type: Article
Times cited : (13)

References (22)
  • 3
    • 79959807548 scopus 로고    scopus 로고
    • While this paper was under review, a report by Grainger and co-workers describing their own investigation into the bromination of indole-3-carboxylate appeared, available online 14.05.2011 doi:10.1039/C1OB05522D
    • While this paper was under review, a report by Grainger and co-workers describing their own investigation into the bromination of indole-3-carboxylate appeared: Parsons, T. B.; Ghellamallah, C.; Male, L.; Spencer, N.; Grainger, R. S. Org. Biomol. Chem. 2011, doi:10.1039/C1OB05522D, available online 14.05.2011.
    • (2011) Org. Biomol. Chem.
    • Parsons, T.B.1    Ghellamallah, C.2    Male, L.3    Spencer, N.4    Grainger, R.S.5
  • 4
    • 79959872805 scopus 로고    scopus 로고
    • For alternatamides A-C (1-3), the stereochemistry of the N-methylleucine side chain was confirmed as l (2′S) by degradation studies. The l-configuration of the N-methylleucine in alternatamide D (4) is assumed.
    • For alternatamides A-C (1-3), the stereochemistry of the N-methylleucine side chain was confirmed as l (2′S) by degradation studies. The l-configuration of the N-methylleucine in alternatamide D (4) is assumed.
  • 13
    • 79959897859 scopus 로고    scopus 로고
    • 6-Nitroindoline costs >NZ$220 for 5 g (Sigma-Aldrich®).
    • 6-Nitroindoline costs >NZ$220 for 5 g (Sigma-Aldrich®).
  • 20
    • 79959909470 scopus 로고    scopus 로고
    • There are limited examples of N-methylleucine being used in amide couplings with an amine coupling partner. For one example US Patent, 20100323994, 2009
    • There are limited examples of N-methylleucine being used in amide couplings with an amine coupling partner. For one example, see: Fink, B. E.; Chen, L.; Chen, P.; Dodd, D. S.; Gaval, A. V.; Kim, S.-H.; Vaccaro, W.; Zhang, L. H. US Patent, 20100323994, 2009; Chem. Abstr. 2009, 151, 245681.
    • (2009) Chem. Abstr. , vol.151 , pp. 245681
    • Fink, B.E.1    Chen, L.2    Chen, P.3    Dodd, D.S.4    Gaval, A.V.5    Kim, S.-H.6    Vaccaro, W.7    Zhang, L.H.8
  • 21
    • 79959866796 scopus 로고    scopus 로고
    • The coupling of the free base 5 with 11 led to poor yields (20-30%) of the desired amide product. Thus, the hydrochloride salt 5·HCl was used as the amine coupling partner to ensure good yields.
    • The coupling of the free base 5 with 11 led to poor yields (20-30%) of the desired amide product. Thus, the hydrochloride salt 5·HCl was used as the amine coupling partner to ensure good yields.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.