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Volumn 6, Issue 18, 2004, Pages 3203-3206

Total synthesis of (-)-callystatin A

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BROMINE DERIVATIVE; CALLYSTATIN A; LACTONE; TRIACYLGLYCEROL LIPASE; VINYL DERIVATIVE;

EID: 4544263102     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048664r     Document Type: Article
Times cited : (71)

References (39)
  • 3
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    • (b) For a discussion of the biological activity of (-)-callystatin A, leptomycin, and related compounds, see: Kalesse, M.; Christmann, M. Synthesis 2002, 981-1003.
    • (2002) Synthesis , pp. 981-1003
    • Kalesse, M.1    Christmann, M.2
  • 14
    • 0037033189 scopus 로고    scopus 로고
    • For additional studies toward fragment synthesis, see: (a) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 185-187. (b) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 1593. (c) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 8883-8885.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 185-187
    • Dias, L.C.1    Meira, P.R.R.2
  • 15
    • 0037127487 scopus 로고    scopus 로고
    • For additional studies toward fragment synthesis, see: (a) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 185-187. (b) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 1593. (c) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 8883-8885.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 1593
    • Dias, L.C.1    Meira, P.R.R.2
  • 16
    • 0037010820 scopus 로고    scopus 로고
    • For additional studies toward fragment synthesis, see: (a) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 185-187. (b) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 1593. (c) Dias, L. C.; Meira, P. R. R. Tetrahedron Lett. 2002, 43, 8883-8885.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 8883-8885
    • Dias, L.C.1    Meira, P.R.R.2
  • 18
    • 4544301309 scopus 로고    scopus 로고
    • Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, Chapter 1
    • (a) Negishi, E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 1.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions
    • Negishi, E.1
  • 24
    • 4544367112 scopus 로고    scopus 로고
    • note
    • Pseudomonas AK lipase was purchased from Amano International Enzyme Co.
  • 25
    • 4544314430 scopus 로고    scopus 로고
    • note
    • The ee of recovered (S)-10 was >95%. See the Supporting Information for full characterization and the stereochemical assignments of 5 and 15.
  • 33
    • 4544289952 scopus 로고    scopus 로고
    • note
    • Hydroxy aldehyde (21, R = H) displayed similar reactivity.
  • 35
    • 4544378757 scopus 로고    scopus 로고
    • note
    • Unusual reactivity of similar intermediates has been reported. See refs 4a,e,f and 5b for details.
  • 36
    • 0041350417 scopus 로고    scopus 로고
    • For application in related ene-yne systems, see: Shi, J.; Zeng, X.; Negishi, E. Org. Lett. 2003, 5, 1825-1828.
    • (2003) Org. Lett. , vol.5 , pp. 1825-1828
    • Shi, J.1    Zeng, X.2    Negishi, E.3
  • 38
    • 0000906771 scopus 로고
    • For a discussion of electronic effects in Pd-mediated cross-couplings, see: Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047-1062.
    • (1994) Chem. Rev. , vol.94 , pp. 1047-1062
    • Grushin, V.V.1    Alper, H.2
  • 39
    • 4544292928 scopus 로고    scopus 로고
    • note
    • Reproducibly, iodide 29 was recovered in 20-30% yield from this reaction. Attempts to increase iodide conversion to desired coupling product were unsuccessful.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.