메뉴 건너뛰기




Volumn 75, Issue 2-3, 2003, Pages 235-249

Progress in fumagillin synthesis

Author keywords

[No Author keywords available]

Indexed keywords

FUMAGILLOL CHLOROACETYLCARBAMATE;

EID: 0037317481     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200375020235     Document Type: Conference Paper
Times cited : (15)

References (46)
  • 7
    • 0028933562 scopus 로고
    • (a) For other TNP-470 derivatives, see: S. Marui, T. Yamamoto, K. Sudo, H. Akimoto, S. Kishimoto. Chem. Pharm. Bull. 43, 588 (1995); (b) N. Sin, L. Meng, M. Q. W. Wang, J. J. Wen, W. G. Bornmann, C. M. Crews. Proc. Natl. Acad. Sci. USA 94, 6099 (1997); (c) E. C. Griffith, Z. Su, S. Niwayama, C. A. Ramsey, Y. H. Chang, J. O. Liu. Proc. Natl. Acad. Sci. USA 95, 15183 (1998); (d) C. K. Han, S. K. Ahn, N. S. Choi, R. K. Hong, S. K. Moon, H. K. Chun, S. J. Lee, J. W. Kim, C. I. Hong, D. Kim, J. H. Yoon, K. T. No. Bioorg. Med. Chem. 10, 39 (2000).
    • (1995) Chem. Pharm. Bull. , vol.43 , pp. 588
    • Marui, S.1    Yamamoto, T.2    Sudo, K.3    Akimoto, H.4    Kishimoto, S.5
  • 8
    • 0030924753 scopus 로고    scopus 로고
    • (a) For other TNP-470 derivatives, see: S. Marui, T. Yamamoto, K. Sudo, H. Akimoto, S. Kishimoto. Chem. Pharm. Bull. 43, 588 (1995); (b) N. Sin, L. Meng, M. Q. W. Wang, J. J. Wen, W. G. Bornmann, C. M. Crews. Proc. Natl. Acad. Sci. USA 94, 6099 (1997); (c) E. C. Griffith, Z. Su, S. Niwayama, C. A. Ramsey, Y. H. Chang, J. O. Liu. Proc. Natl. Acad. Sci. USA 95, 15183 (1998); (d) C. K. Han, S. K. Ahn, N. S. Choi, R. K. Hong, S. K. Moon, H. K. Chun, S. J. Lee, J. W. Kim, C. I. Hong, D. Kim, J. H. Yoon, K. T. No. Bioorg. Med. Chem. 10, 39 (2000).
    • (1997) Proc. Natl. Acad. Sci. USA , vol.94 , pp. 6099
    • Sin, N.1    Meng, L.2    Wang, M.Q.W.3    Wen, J.J.4    Bornmann, W.G.5    Crews, C.M.6
  • 9
    • 13044300888 scopus 로고    scopus 로고
    • (a) For other TNP-470 derivatives, see: S. Marui, T. Yamamoto, K. Sudo, H. Akimoto, S. Kishimoto. Chem. Pharm. Bull. 43, 588 (1995); (b) N. Sin, L. Meng, M. Q. W. Wang, J. J. Wen, W. G. Bornmann, C. M. Crews. Proc. Natl. Acad. Sci. USA 94, 6099 (1997); (c) E. C. Griffith, Z. Su, S. Niwayama, C. A. Ramsey, Y. H. Chang, J. O. Liu. Proc. Natl. Acad. Sci. USA 95, 15183 (1998); (d) C. K. Han, S. K. Ahn, N. S. Choi, R. K. Hong, S. K. Moon, H. K. Chun, S. J. Lee, J. W. Kim, C. I. Hong, D. Kim, J. H. Yoon, K. T. No. Bioorg. Med. Chem. 10, 39 (2000).
    • (1998) Proc. Natl. Acad. Sci. USA , vol.95 , pp. 15183
    • Griffith, E.C.1    Su, Z.2    Niwayama, S.3    Ramsey, C.A.4    Chang, Y.H.5    Liu, J.O.6
  • 10
    • 0001462209 scopus 로고    scopus 로고
    • (a) For other TNP-470 derivatives, see: S. Marui, T. Yamamoto, K. Sudo, H. Akimoto, S. Kishimoto. Chem. Pharm. Bull. 43, 588 (1995); (b) N. Sin, L. Meng, M. Q. W. Wang, J. J. Wen, W. G. Bornmann, C. M. Crews. Proc. Natl. Acad. Sci. USA 94, 6099 (1997); (c) E. C. Griffith, Z. Su, S. Niwayama, C. A. Ramsey, Y. H. Chang, J. O. Liu. Proc. Natl. Acad. Sci. USA 95, 15183 (1998); (d) C. K. Han, S. K. Ahn, N. S. Choi, R. K. Hong, S. K. Moon, H. K. Chun, S. J. Lee, J. W. Kim, C. I. Hong, D. Kim, J. H. Yoon, K. T. No. Bioorg. Med. Chem. 10, 39 (2000).
    • (2000) Bioorg. Med. Chem. , vol.10 , pp. 39
    • Han, C.K.1    Ahn, S.K.2    Choi, N.S.3    Hong, R.K.4    Moon, S.K.5    Chun, H.K.6    Lee, S.J.7    Kim, J.W.8    Hong, C.I.9    Kim, D.10    Yoon, J.H.11    No, K.T.12
  • 24
    • 0013122191 scopus 로고    scopus 로고
    • note
    • However, in some fumagillin analogs, which displayed in vivo antitumor activity, the spiro epoxide is transformed into a hydroxy methylenesulfonium derivative, see ref. 7a.
  • 25
    • 0013166807 scopus 로고    scopus 로고
    • note
    • For clarity, the fumagillin numbering has systematically been used.
  • 27
    • 0037041597 scopus 로고    scopus 로고
    • For recent accounts of Claisen-Ireland rearrangements, see: (a) Y. Chai, S-p. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh. Tetrahedron 58, 2905 (2002); (b) D. Enders, M. Knopp, R. Schiffers. Tetrahedron: Asymmetry 7, 1847 (1996); (c) J. S. Panek, S. Schaus, C. E. Masse. Chemtracts: Org. Chem. 8, 238 (1995).
    • (2002) Tetrahedron , vol.58 , pp. 2905
    • Chai, Y.1    Hong, S.-P.2    Lindsay, H.A.3    McFarland, C.4    McIntosh, M.C.5
  • 28
    • 0030200756 scopus 로고    scopus 로고
    • For recent accounts of Claisen-Ireland rearrangements, see: (a) Y. Chai, S-p. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh. Tetrahedron 58, 2905 (2002); (b) D. Enders, M. Knopp, R. Schiffers. Tetrahedron: Asymmetry 7, 1847 (1996); (c) J. S. Panek, S. Schaus, C. E. Masse. Chemtracts: Org. Chem. 8, 238 (1995).
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 1847
    • Enders, D.1    Knopp, M.2    Schiffers, R.3
  • 29
    • 0037041597 scopus 로고    scopus 로고
    • For recent accounts of Claisen-Ireland rearrangements, see: (a) Y. Chai, S-p. Hong, H. A. Lindsay, C. McFarland, M. C. McIntosh. Tetrahedron 58, 2905 (2002); (b) D. Enders, M. Knopp, R. Schiffers. Tetrahedron: Asymmetry 7, 1847 (1996); (c) J. S. Panek, S. Schaus, C. E. Masse. Chemtracts: Org. Chem. 8, 238 (1995).
    • (1995) Chemtracts: Org. Chem. , vol.8 , pp. 238
    • Panek, J.S.1    Schaus, S.2    Masse, C.E.3
  • 30
    • 0013124338 scopus 로고    scopus 로고
    • note
    • Alternatively, it was possible to prepare an enantiomeric lactone of 22 with an E-double bond on side chain. Rearrangement of this lactone could give rise to a diastereomer of 27 with natural configuration at C4 and unnatural at C3. Inversion of configuration at C3 as in previous syntheses could then be realized. However, the lengthy preparation of lactone 22 [26] was a major drawback for the use of this alternative.
  • 31
    • 0013076445 scopus 로고    scopus 로고
    • Ph.D. thesis, Université de Paris-Sud, Orsay, 18 January
    • W. Picoul. Ph.D. thesis, Université de Paris-Sud, Orsay, 18 January 2001.
    • (2001)
    • Picoul, W.1
  • 32
    • 0344006321 scopus 로고    scopus 로고
    • For reviews on olefin metathesis, see: (a) A. Fürstner. Angew. Chem., Int. Ed. 39, 3012 (2000); (b) R. H. Grubbs and C. Sukbok. Tetrahedron 54, 4413 (1998).
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3012
    • Fürstner, A.1
  • 33
    • 0032580376 scopus 로고    scopus 로고
    • For reviews on olefin metathesis, see: (a) A. Fürstner. Angew. Chem., Int. Ed. 39, 3012 (2000); (b) R. H. Grubbs and C. Sukbok. Tetrahedron 54, 4413 (1998).
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Sukbok, C.2
  • 42
    • 0013170367 scopus 로고    scopus 로고
    • note
    • Minor diastereomers were eliminated at this stage during ester purification.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.