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Volumn 125, Issue 44, 2003, Pages 13531-13540

A Cycloaddition Cascade Approach to the Total Synthesis of (-)-FR182877

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION;

EID: 0242330782     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037643+     Document Type: Article
Times cited : (116)

References (54)
  • 7
    • 0036773510 scopus 로고    scopus 로고
    • The acetylated pachyclavulariaenones D-F are not cytotoxic, in contrast to potent pachyclavulariaenone G having all three hydroxyls free. Susceptible cell lines were P-388 and HT-29; however, no comment is made on mechanism of action. See: Wang, G.-H.; Sheu, J.-H.; Duh, C.-Y.; Chiang, M. Y. J. Nat. Prod. 2002, 65, 1475.
    • (2002) J. Nat. Prod. , vol.65 , pp. 1475
    • Wang, G.-H.1    Sheu, J.-H.2    Duh, C.-Y.3    Chiang, M.Y.4
  • 8
    • 0242369947 scopus 로고    scopus 로고
    • note
    • A comparison of MM2 minimized space-filling models of pachyclavulariaenone G and (-)- FR182877 using Spartan showed considerable homology in size, shape, and disposition of polar functionality between the two natural products (Evans and Starr, unpublished).
  • 16
    • 0242369950 scopus 로고    scopus 로고
    • http://www.dcso.polytechnique.fr/f1-032equipe-htm
    • The following investigators have indicated their efforts toward FR182877 via the Internet: Clarke (http://www.nottingham.ac.uk/~pczpac1/research-web/synthesis.html), Prunet (http://www.dcso.polytechnique.fr/f1-032equipe-htm).
  • 27
    • 0012016624 scopus 로고
    • Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77; J. Am. Chem. Soc. 1981, 103, 2127.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 2127
  • 30
    • 0242369951 scopus 로고    scopus 로고
    • note
    • Complete cis-trans isomerization was observed after storing the neat unpurified reaction product for 24 h.
  • 38
    • 0000903259 scopus 로고
    • First Suzuki coupling with vinyldibromide: Roush, W. R.; Riva, R. J. Org. Chem. 1988, 53, 710.
    • (1988) J. Org. Chem. , vol.53 , pp. 710
    • Roush, W.R.1    Riva, R.2
  • 50
    • 0242369946 scopus 로고    scopus 로고
    • note
    • y coefficients were 0 ± 0.05 for both the HOMO and the LUMO of the indicated atoms.
  • 51
    • 0242307045 scopus 로고    scopus 로고
    • note
    • Dihedral angle constraints were used for all PM3 calculations as follows: O(ester CO)=CI-C2=C3, 180°; C2=C3-C4=C5, 180°; C9=C10-C11=C12, 0°. Interatomic distance contraints were applied to C5-C9 and C4-C12 at distances indicated in the text for the individual experiments.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.