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Volumn 74, Issue 21, 2009, Pages 8143-8153

Design and synthesis of lamellarin D analogues targeting topoisomerase I

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; CHEMICAL EQUATIONS; ELECTROPHILIC SUBSTITUTIONS; KEY REACTIONS; LAMELLARINS; LITHIATION; PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS; PALLADIUM-CATALYZED CROSS-COUPLINGS; REGIO-SELECTIVE; SYNTHETIC ROUTES; TOPOISOMERASE I;

EID: 70350733553     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901589e     Document Type: Article
Times cited : (95)

References (86)
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    • Waring, M., Ed.; RSC Publishing: Cambridge, U.K., Chapter 3
    • (b) Dias, M.; Bailly, C. In Sequence-specific DNA Binding Agents; Waring, M., Ed.; RSC Publishing: Cambridge, U.K., 2006; Chapter 3; pp 44-68.
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    • note
    • According to ref 11, the lamellarin D-DNA-topoisomerase I ternary complex model shown in Figure 1 was reproduced by means of MOE program (Chemical Computing Group Inc.).
  • 63
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    • note
    • Bromination of 9 with 1.0 equiv of NBS in DMF afforded monobromide I in 93% yield, whereas bromination with 2.0 equiv of NBS yielded dibromide II in 97% yield. These results suggest relative reactivity of the pyrrole ring and the pendant aromatic ring against elecrophilic reagents.
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    • For PIFA-mediated cyclization, coupling, and functionalization of pyrroles, see: (a)
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    • The SET from aromatic ring to PIFA is sensitive to the steric hindrance of the aromatic substrate, see
    • The SET from aromatic ring to PIFA is sensitive to the steric hindrance of the aromatic substrate, see: Dohi, T.; Ito, M.; Morimoto, K.; Iwata, M.; Kita, Y. Angew. Chem., Int. Ed. 2008, 47, 1301-1304.
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 1301-1304
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    • note
    • DFT calculation of 22 indicated high atomic charge and extended HOMO at the C-1 position. The calculation suggested that electrophilic substitution reaction could occur at C-1 selectively. See Supporting Information.


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