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Volumn 69, Issue 17, 2004, Pages 5638-5645

Highly diastereoselective approach toward (±)-tetraponerine T6 and analogues via the double cycloisomerization-reduction of bis-alkynylpyrimidines

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; HYDROGENATION; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS (CHEMICAL);

EID: 4043175420     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049259g     Document Type: Article
Times cited : (52)

References (27)
  • 10
    • 0000509322 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York
    • (b) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, p 521.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 521
    • Sonogashira, K.1
  • 16
    • 0037059436 scopus 로고    scopus 로고
    • For lower thermal stability of the terminal allenic intermediates, see ref 1 and: Kel'in, A. V.; Gevorgyan, V. J. Org. Chem. 2002, 67, 95.
    • (2002) J. Org. Chem. , vol.67 , pp. 95
    • Kel'in, A.V.1    Gevorgyan, V.2
  • 17
    • 0000409291 scopus 로고
    • The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York
    • For hydrogenation of pyrimidines, see: (a) Brown, D. J. The Pyrimidines; The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 1994; Vol. 52, pp 790-793.
    • (1994) The Pyrimidines , vol.52 , pp. 790-793
    • Brown, D.J.1
  • 18
    • 0004138793 scopus 로고
    • The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York
    • (b) Brown, D. J. The Pyrimidines Supplement I; The Chemistry of Heterocyclic Compounds; John Wiley & Sons: New York, 1970; pp 337-341.
    • (1970) The Pyrimidines Supplement I , pp. 337-341
    • Brown, D.J.1
  • 19
    • 4043115763 scopus 로고    scopus 로고
    • note
    • 13C NMR analysis of the crude material revealed that 11d was formed as a single diastereomer. The relative configuration of its stereogenic centers was assigned by NOE experiment after the subsequent reduction step.
  • 20
    • 0034803515 scopus 로고    scopus 로고
    • For stereoelectronic control in addition of nucleophiles to an amidinium ion, see: (a) Perrin, C. L.; Young, D. B. J. Am. Chem. Soc. 2001, 123, 4451.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 4451
    • Perrin, C.L.1    Young, D.B.2
  • 22
    • 0004293179 scopus 로고    scopus 로고
    • Oxford Chemistry Primer 36; Oxford University Press: Oxford
    • (c) Kirby, A. J. Stereoelectronic effects; Oxford Chemistry Primer 36; Oxford University Press: Oxford, 1996, pp 54-55.
    • (1996) Stereoelectronic Effects , pp. 54-55
    • Kirby, A.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.