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Volumn 10, Issue 10, 2012, Pages 2126-2132

Pyrazine alkaloids via dimerization of amino acid-derived α-amino aldehydes: Biomimetic synthesis of 2,5-diisopropylpyrazine, 2,5-bis(3- indolylmethyl)pyrazine and actinopolymorphol C

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ALDEHYDES; BIOMIMETIC SYNTHESIS; IN-SITU; NATURAL PRODUCTS; ONE POT; PYRAZINES; REACTION SOLVENTS;

EID: 84857591048     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c2ob06935k     Document Type: Article
Times cited : (19)

References (96)
  • 45
    • 0042309739 scopus 로고    scopus 로고
    • in, ed. G. A. Reineccius and T. A. Reineccius, ACS, Washington, p. 132. The synthesis of pyrazines generally relies on reactions outlined in references 14-16 Condensation of a 1,2-dicarbonyl with a 1,2-diamine
    • G. P. Rizzi, in Heteroaromatic Aroma Compounds, ed., G. A. Reineccius, and, T. A. Reineccius, ACS, Washington, 2002, vol. 826, p. 132.
    • (2002) Heteroaromatic Aroma Compounds , vol.826
    • Rizzi, G.P.1
  • 77
    • 67349244742 scopus 로고    scopus 로고
    • To the best of our knowledge, the intermolecular cyclization of d-glucosamine is the only literature example that bears any resemblance the α-amino aldehyde dimerization proposed in Scheme 5
    • D. C. Robacker M. Aluja R. J. Bartelt J. Patt J. Chem. Ecol. 2009 35 601
    • (2009) J. Chem. Ecol. , vol.35 , pp. 601
    • Robacker, D.C.1    Aluja, M.2    Bartelt, R.J.3    Patt, J.4
  • 91
    • 84857594122 scopus 로고    scopus 로고
    • Ph.D Thesis, North Carolina State University, See the ESI for full details
    • B. M. Cash, Ph.D Thesis, North Carolina State University, 2010
    • (2010)
    • Cash, B.M.1
  • 96
    • 0344420052 scopus 로고    scopus 로고
    • Schulz suggested that a (possibly enzymatic) rearrangement during condensation of two α-amino aldehyde units 23 forms the basis of the biosynthesis of 2,6-diisopropylpyrazine. However, in all our biomimetic α-amino aldehyde dimerizations, only the 2,5-disubstituted regioisomer (10, 11 and 12) was ever observed
    • M. Nakamura H. Miyashita M. Yamaguchi Y. Shirasaki Y. Nakamura J. Inoue Bioorg. Med. Chem. 2003 11 5449
    • (2003) Bioorg. Med. Chem. , vol.11 , pp. 5449
    • Nakamura, M.1    Miyashita, H.2    Yamaguchi, M.3    Shirasaki, Y.4    Nakamura, Y.5    Inoue, J.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.