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Volumn 127, Issue 13, 2005, Pages 4596-4598

Total synthesis of cribrostatin IV: Fine-tuning the character of an amide bond by remote control

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CRIBROSTATIN IV; STATIN; UNCLASSIFIED DRUG;

EID: 16844386126     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050203t     Document Type: Article
Times cited : (94)

References (36)
  • 8
    • 0141519496 scopus 로고    scopus 로고
    • For an elegant solution to reaching the C3-C4 olefin series bearing the C21 lactam, see: Jin, W.; Metobo, S.; Williams, R. M. Org. Lett. 2003, 5, 2095. For a particularly concise route to saframycin, see: Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828.
    • (2003) Org. Lett. , vol.5 , pp. 2095
    • Jin, W.1    Metobo, S.2    Williams, R.M.3
  • 9
    • 0033601117 scopus 로고    scopus 로고
    • For an elegant solution to reaching the C3-C4 olefin series bearing the C21 lactam, see: Jin, W.; Metobo, S.; Williams, R. M. Org. Lett. 2003, 5, 2095. For a particularly concise route to saframycin, see: Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 10828
    • Myers, A.G.1    Kung, D.W.2
  • 22
    • 16844372677 scopus 로고    scopus 로고
    • note
    • Attempts to perform the Jeffery-Heck reaction directly with dehydroalanine gave lower yields due to polymerization. Accordingly, precursor 14 was used, and the requisite dehydroalanine was formed in situ.
  • 23
    • 0034611483 scopus 로고    scopus 로고
    • For previous examples of connecting the subunits by amide bond formation to a secondary amine, see: (a) Martinez, E. J.; Corey, E. J. Org. Lett. 2000, 2, 993.
    • (2000) J. Org. Lett. , vol.2 , pp. 993
    • Martinez, E.J.1    Corey, E.2
  • 26
    • 16844375266 scopus 로고    scopus 로고
    • note
    • 11 relationship emerges syn. A full account of this remote control element will be provided shortly.
  • 32
    • 16844385192 scopus 로고    scopus 로고
    • note
    • 21 bond cleavage in some products.
  • 34
    • 0017397793 scopus 로고
    • The notion of the reductive unveiling of drug-like activity from bioactivatable pro-drugs was globally summarized in 1977: Moore, H. W. Science 1977, 197, 527. For a summary of its pertinence to the mitomycins, see: Danishefsky, S. J.; Schkeryantz, J. M. Synlett 1995, 475.
    • (1977) Science , vol.197 , pp. 527
    • Moore, H.W.1
  • 35
    • 0002080857 scopus 로고
    • The notion of the reductive unveiling of drug-like activity from bioactivatable pro-drugs was globally summarized in 1977: Moore, H. W. Science 1977, 197, 527. For a summary of its pertinence to the mitomycins, see: Danishefsky, S. J.; Schkeryantz, J. M. Synlett 1995, 475.
    • (1995) Synlett , pp. 475
    • Danishefskyn, S.J.1    Schkeryantz, J.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.