메뉴 건너뛰기




Volumn 2010, Issue 3, 2010, Pages 7-14

Application of the PIFA-mediated alkyne amidation reaction to the formal synthesis of (±)-clausenamide

Author keywords

Clausenamide; Cyclization; Hypervalent iodine; Pyrrolidinone

Indexed keywords


EID: 77953429830     PISSN: 15517012     EISSN: 15517004     Source Type: None    
DOI: 10.3998/ark.5550190.0011.302     Document Type: Article
Times cited : (9)

References (45)
  • 1
    • 0036628555 scopus 로고    scopus 로고
    • For recent reviews on the synthetic applications of polyvalent iodine reagents, see: a
    • For recent reviews on the synthetic applications of polyvalent iodine reagents, see: (a) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
    • (2002) J. Chem. Rev. , vol.102 , pp. 2523
    • Zhdankin, V.V.1    Stang, P.2
  • 7
    • 0001901623 scopus 로고
    • For reviews concerning the chemistry of nitrenium ions, see: a, In, Scriven, E. F. V.; Ed.; Academic Press: Orlando
    • For reviews concerning the chemistry of nitrenium ions, see: (a) Abramovitch, R. A.; Jeyaraman, R. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V.; Ed.; Academic Press: Orlando, 1984; p 297.
    • (1984) Azides and Nitrenes: Reactivity and Utility , pp. 297
    • Abramovitch, R.A.1    Jeyaraman, R.2
  • 8
    • 33646240303 scopus 로고    scopus 로고
    • Moss, R. A., Platz, M. S., Jones, M., Eds.; Wiley-Interscience: Hoboken, NJ
    • (b) Falvey, D. E. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S., Jones, M., Eds.; Wiley-Interscience: Hoboken, NJ, 2004; p 594.
    • (2004) Reactive Intermediate Chemistry , pp. 594
    • Falvey, D.E.1
  • 21
    • 77953435515 scopus 로고    scopus 로고
    • Clausenamide is isolated from the natural media as a racemate
    • Clausenamide is isolated from the natural media as a racemate.
  • 28
    • 77953413513 scopus 로고    scopus 로고
    • Chen, S. Patent 2003, EP 1348696
    • (a) Zhang, J. -T.; Huang, L.; Wu, K.; Chen, S. Patent 2003, EP 1348696 (Chem. Abstr. 2003, 139, 292098).
    • (2003) (Chem. Abstr , vol.139 , pp. 292098
    • Zhang, J.-T.1    Huang, L.2    Wu, K.3
  • 31
    • 77953414623 scopus 로고    scopus 로고
    • Chem. Abstr. 2002, 137, 363098.
    • (2002) Chem. Abstr , vol.137 , pp. 363098
  • 32
    • 0344010056 scopus 로고    scopus 로고
    • For previous syntheses of this compound, see: a
    • For previous syntheses of this compound, see: (a) Yan, Z.; Wang, J.; Tian, W. Tetrahedron Lett. 2003, 44, 9383.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 9383
    • Yan, Z.1    Wang, J.2    Tian, W.3
  • 37
    • 77953405718 scopus 로고    scopus 로고
    • Easily prepared from pentynoic acid by amide formation followed by a Sonogashira coupling step
    • Easily prepared from pentynoic acid by amide formation followed by a Sonogashira coupling step.
  • 38
    • 0346970844 scopus 로고    scopus 로고
    • 2OH was crucial for the success of the reaction. For a revision about the chemical properties and synthetic uses of trifluoroethanol and other related solvents, see
    • 2OH was crucial for the success of the reaction. For a revision about the chemical properties and synthetic uses of trifluoroethanol and other related solvents, see: Bégué, J. -P.; Bonnet-Delpon, D.; Crousse, B. Synlett 2004, 18.
    • (2004) Synlett , pp. 18
    • Bégué, J.-P.1    Bonnet-Delpon, D.2    Crousse, B.3
  • 39
    • 17444397444 scopus 로고    scopus 로고
    • N-Methoxyamides and N-phthalimidoamides are also known to generate stable acyl-nitrenium intermediates. a
    • N-Methoxyamides and N-phthalimidoamides are also known to generate stable acyl-nitrenium intermediates. (a) Falvey, D. E.; Kung, A. C. J. Org. Chem. 2005, 70, 3127.
    • (2005) J. Org. Chem. , vol.70 , pp. 3127
    • Falvey, D.E.1    Kung, A.C.2
  • 43
    • 77953408978 scopus 로고    scopus 로고
    • All efforts to improve the stereoselectivity of the cyclization step by modification of the cyclization conditions were negative. In addition, attempts to achieve a bigger quantity of the desired isomer by chemical isomerization of pyrrolidinone 10trans were unproductive, which probably accounts for the higher thermodynamic stability of such isomer
    • All efforts to improve the stereoselectivity of the cyclization step by modification of the cyclization conditions were negative. In addition, attempts to achieve a bigger quantity of the desired isomer by chemical isomerization of pyrrolidinone 10trans were unproductive, which probably accounts for the higher thermodynamic stability of such isomer.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.