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Volumn 74, Issue 15, 2009, Pages 5730-5733

Syntheses of carbocyclic uracil polyoxin C analogs: Application of Pd(0)/InI-allylation of 4-acetoxy-2-azetidinone

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLATION; CYCLOADDUCT; HETERO-DIELS; SIDE CHAINS;

EID: 68049114668     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900861x     Document Type: Article
Times cited : (22)

References (36)
  • 1
    • 0032969007 scopus 로고    scopus 로고
    • For a review of synthetic methods, see
    • For a review of synthetic methods, see: Zhang, D.; Miller, M. J. Curr. Pharm. Design 1999, 5, 73-99.
    • (1999) Curr. Pharm. Design , vol.5 , pp. 73-99
    • Zhang, D.1    Miller, M.J.2
  • 25
    • 0032950817 scopus 로고    scopus 로고
    • For a detailed preparation of acyl isocyanate 6, refer to experimental section or see: Santana, L.; Teijeira, M.; Uriarte, E. J. Heterocyclic Chem. 1999, 36, 293-295.
    • For a detailed preparation of acyl isocyanate 6, refer to experimental section or see: Santana, L.; Teijeira, M.; Uriarte, E. J. Heterocyclic Chem. 1999, 36, 293-295.
  • 29
    • 68049106765 scopus 로고    scopus 로고
    • For preparation of N-methylthiophthalimide 9, refer to Supporting Information.
    • For preparation of N-methylthiophthalimide 9, refer to Supporting Information.
  • 30
    • 33646485245 scopus 로고    scopus 로고
    • Recently, a class of N-alkylthio b-lactams demonstrated anticancer activity. For recent examples of N-alkylthio β-lactams as anticancer agents, see: (a) Kuhn, D. J.; Wang, Y.; Minic, V.; Coates, C.; Reddy; Kumar, G.; Daniel, K. G.; Shim, J.-Y.; Chen, D.; Landis-Piwowar, K. R.; Miller, F. R.; Turos, E.; Dou, Q. P. Front. Biosci. 2005, 10, 1183-1190.
    • Recently, a class of N-alkylthio b-lactams demonstrated anticancer activity. For recent examples of N-alkylthio β-lactams as anticancer agents, see: (a) Kuhn, D. J.; Wang, Y.; Minic, V.; Coates, C.; Reddy; Kumar, G.; Daniel, K. G.; Shim, J.-Y.; Chen, D.; Landis-Piwowar, K. R.; Miller, F. R.; Turos, E.; Dou, Q. P. Front. Biosci. 2005, 10, 1183-1190.
  • 33
    • 0028589329 scopus 로고    scopus 로고
    • 4-mediated dihydroxylation occurs from opposite face of the allylic methine protons and syn-tetrasubstituted cyclopentanes result. For compound 8, J=6.8 Hz and all syn diastereomer 1b was obtained as the major product after dihydroxylation. For an explanation of how 1,4-disubstituted cyclopentene conformations are determined from coupling constants, see: Katagiri, N.; Ito, Y.; Kitano, K.; Toyota, A.; Kaneko, C. Chem. Pharm. Bull. 1994, 42, 2653-2633.
    • 4-mediated dihydroxylation occurs from opposite face of the allylic methine protons and syn-tetrasubstituted cyclopentanes result. For compound 8, J=6.8 Hz and all syn diastereomer 1b was obtained as the major product after dihydroxylation. For an explanation of how 1,4-disubstituted cyclopentene conformations are determined from coupling constants, see: Katagiri, N.; Ito, Y.; Kitano, K.; Toyota, A.; Kaneko, C. Chem. Pharm. Bull. 1994, 42, 2653-2633.
  • 35
    • 0001672730 scopus 로고    scopus 로고
    • 4 dihydroxylation, see: Corey, E. J.; Das, J. Tetrahedron Lett. 1982, 23, 4217-4220.
    • 4 dihydroxylation, see: Corey, E. J.; Das, J. Tetrahedron Lett. 1982, 23, 4217-4220.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.