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Volumn 11, Issue 6, 2009, Pages 1341-1344

Total synthesis of (±)-agelastatin A, A potent inhibitor of osteopontin-mediated neoplastic transformations

Author keywords

[No Author keywords available]

Indexed keywords

AGELASTATIN A; ALKALOID; ANTINEOPLASTIC AGENT; BIOLOGICAL PRODUCT; OSTEOPONTIN; OXAZOLIDINONE DERIVATIVE;

EID: 64049086842     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900133v     Document Type: Article
Times cited : (60)

References (56)
  • 2
    • 0141742509 scopus 로고    scopus 로고
    • For recent reviews of synthetic efforts towards pyrrole-imidazole alkaloids, see: a
    • For recent reviews of synthetic efforts towards pyrrole-imidazole alkaloids, see: (a) Hoffmann, H.; Lindel, T. Synthesis 2003, 1753.
    • (2003) Synthesis , pp. 1753
    • Hoffmann, H.1    Lindel, T.2
  • 16
    • 64549130136 scopus 로고    scopus 로고
    • 6, p 352
    • 6, p 352.
  • 18
    • 52149088558 scopus 로고    scopus 로고
    • Osteopontin is an extracellular structural glycoprotein implicated in playing a fundamental role in mediating tumor metastasis: Weber, G. F. Cancer Lett. 2008, 270, 181
    • Osteopontin is an extracellular structural glycoprotein implicated in playing a fundamental role in mediating tumor metastasis: Weber, G. F. Cancer Lett. 2008, 270, 181.
  • 19
    • 64549095677 scopus 로고    scopus 로고
    • For a review of these efforts, see ref 2b
    • For a review of these efforts, see ref 2b.
  • 28
    • 61349122654 scopus 로고    scopus 로고
    • For a related approach, see
    • (a) Yoshimitsu, T.; Ino, T.; Tanaka, T. Org. Lett. 2008, 10, 5457. For a related approach, see:
    • (2008) Org. Lett , vol.10 , pp. 5457
    • Yoshimitsu, T.1    Ino, T.2    Tanaka, T.3
  • 31
    • 0033484123 scopus 로고    scopus 로고
    • For reviews, see: a
    • For reviews, see: (a) Knapp, S. Chem. Soc. Rev. 1999, 28, 61.
    • (1999) Chem. Soc. Rev , vol.28 , pp. 61
    • Knapp, S.1
  • 36
    • 33646064214 scopus 로고    scopus 로고
    • The Allylic Trihaloacetimidate Rearrangement
    • Overman, L. E, Ed, John Wiley and Sons, Inc
    • Overman, L. E.; Carpenter, N. E. The Allylic Trihaloacetimidate Rearrangement. In Organic Reactions; Overman, L. E., Ed.; John Wiley and Sons, Inc., 2005; Vol 66, pp 1-107.
    • (2005) Organic Reactions , vol.66 , pp. 1-107
    • Overman, L.E.1    Carpenter, N.E.2
  • 37
    • 64549137373 scopus 로고    scopus 로고
    • Conventional methods of trichloroacetamide cleavage, include
    • Conventional methods of trichloroacetamide cleavage, include:
  • 51
    • 0027442712 scopus 로고    scopus 로고
    • The success of NBA in mediating the cyclization of 8 may stem from the increased basicity (relative to succinimidyl or halide ions) of the acetamide anion generated upon brominium ion formation, which, through deprotonation, would serve to increase the nucleophilicity of the trichloroacetamide group. The use of NBA also minimizes the halide ion concentration and thus formation of the dihalide addition product: Corey, E. J.; Loh, T. P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600.
    • The success of NBA in mediating the cyclization of 8 may stem from the increased basicity (relative to succinimidyl or halide ions) of the acetamide anion generated upon brominium ion formation, which, through deprotonation, would serve to increase the nucleophilicity of the trichloroacetamide group. The use of NBA also minimizes the halide ion concentration and thus formation of the dihalide addition product: Corey, E. J.; Loh, T. P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600.
  • 54
    • 8844231767 scopus 로고    scopus 로고
    • In our case, it was found that use of NaHCO3 generated product 14 in significantly better yields than either Cs2CO 3 or K2CO3, as previously reported: Urabe, D, Sugino, K, Nishikawa, T, Isobe, M Tetrahedron Lett. 2004, 45, 9405
    • 3, as previously reported: Urabe, D.; Sugino, K.; Nishikawa, T.; Isobe, M Tetrahedron Lett. 2004, 45, 9405.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.