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Volumn 132, Issue 17, 2010, Pages 5926-5927

Total synthesis of (+)-complanadine a using an iridium-catalyzed pyridine C-H functionalization

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ESTERS; C-H FUNCTIONALIZATION; SITE SELECTIVE; TOTAL SYNTHESIS; UNSYMMETRICAL;

EID: 77951687825     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja101893b     Document Type: Article
Times cited : (201)

References (34)
  • 1
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    • For pertinent reviews, see
    • For pertinent reviews, see: Ma, X. and Gang, D. R. Nat. Prod. Rep. 2004, 21, 752
    • (2004) Nat. Prod. Rep. , vol.21 , pp. 752
    • Ma, X.1    Gang, D.R.2
  • 3
    • 50149110201 scopus 로고    scopus 로고
    • 1 st ed.; Wiley-VCH: Weinheim, Germany
    • Hudlicky, T. and Reed, J. W. In The Way of Synthesis, 1 st ed.; Wiley-VCH: Weinheim, Germany, 2007; pp 573 - 602.
    • (2007) The Way of Synthesis , pp. 573-602
    • Hudlicky, T.1    Reed, J.W.2
  • 9
    • 0035727888 scopus 로고    scopus 로고
    • For a leading review, see
    • For a leading review, see: Shigeta, M. and Homma, A. CNS Drug Rev. 2001, 7, 353
    • (2001) CNS Drug Rev. , vol.7 , pp. 353
    • Shigeta, M.1    Homma, A.2
  • 16
    • 77951670239 scopus 로고    scopus 로고
    • The group of Prof. D. Siegel (UT Austin) has also recently completed a synthesis of 4 (personal communication)
    • The group of Prof. D. Siegel (UT Austin) has also recently completed a synthesis of 4 (personal communication).
  • 19
    • 37249064829 scopus 로고    scopus 로고
    • For more details, see the Supporting Information
    • Liu, K.-M., Chau, C.-M., and Sha, C.-K. Chem. Commun. 2008, 91 For more details, see the Supporting Information.
    • (2008) Chem. Commun. , pp. 91
    • Liu, K.-M.1    Chau, C.-M.2    Sha, C.-K.3
  • 20
    • 77951681624 scopus 로고    scopus 로고
    • For ease of handling, air-sensitive ene-imine 10 was generated in situ under the reaction conditions for formation of 17
    • For ease of handling, air-sensitive ene-imine 10 was generated in situ under the reaction conditions for formation of 17.
  • 22
    • 77951682287 scopus 로고    scopus 로고
    • For an improved procedure, see the Supporting Information
    • For an improved procedure, see the Supporting Information.
  • 24
    • 77951688176 scopus 로고    scopus 로고
    • Preliminary results indicated that 13 may be used instead of 9 in the formation of 17
    • Preliminary results indicated that 13 may be used instead of 9 in the formation of 17.
  • 25
    • 77951696268 scopus 로고    scopus 로고
    • Because of its high polarity, 17 was taken directly into the next step without purification
    • Because of its high polarity, 17 was taken directly into the next step without purification.
  • 26
    • 77951690416 scopus 로고    scopus 로고
    • Although pyridone 18 may be brominated at the requisite position, attempts to advance the 3-bromopyridone were unsuccessful
    • Although pyridone 18 may be brominated at the requisite position, attempts to advance the 3-bromopyridone were unsuccessful.
  • 29
    • 77951675557 scopus 로고    scopus 로고
    • 13C NMR spectra of 4
    • 13C NMR spectra of 4.
  • 30
    • 77951690892 scopus 로고    scopus 로고
    • Complanadine A was obtained along with small amounts of N -Boc-lycodine (19), which presumably arises from protodeborylation
    • Complanadine A was obtained along with small amounts of N -Boc-lycodine (19), which presumably arises from protodeborylation.
  • 32
    • 77951680648 scopus 로고
    • (Upjohn). U.S. Patent
    • Schneider, W. P. and McIntosh, A. V. (Upjohn). U.S. Patent 2,769,824, 1956.
    • (1956) , vol.2 , pp. 769-824
    • Schneider, W.P.1    Mcintosh, A.V.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.