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Volumn 4, Issue 20, 2002, Pages 3525-3528

Diazonamide synthesis studies: Use of negishi coupling to fashion diazonamide-related biaryls with defined axial chirality

Author keywords

[No Author keywords available]

Indexed keywords

DIAZONAMIDE A; FUSED HETEROCYCLIC RINGS; OXAZOLE DERIVATIVE;

EID: 0037015445     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026694t     Document Type: Article
Times cited : (41)

References (29)
  • 14
    • 84986437005 scopus 로고
    • 1 = H) using the directed Monte Carlo algorithm of Macromodel 6.5 (cf.: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467) led to a family of four low-energy conformers corresponding to the four possible atropisomers about the indicated biaryl linkages. Two of these species were of equivalently low energy, 3 as shown and its rotomer about the C(24)/C(26) bond. However, only 3 among these conformers brings C(10) and C(30) within bonding distance, 3.51 Å. The enthalpies of rotation about the C(24)/C(25) and C(16)/C(18) bonds were estimated by the difference between the "global minimum" conformer 3 and planar versions of 3 where the relevant biaryl dihedral was locked at either 0° or 180°, The four values obtained (two rotational directions per bond) are shown with 3. Only rotation about the C(24)/C(26) bond in one direction is predicted by this analysis to be facile at room temperature (Δ/H‡ ≈ 14 kcal/mol).
    • (1990) J. Comput. Chem. , vol.11 , pp. 440-467
    • Mohamadi, F.1    Richards, N.G.J.2    Guida, W.C.3    Liskamp, R.4    Lipton, M.5    Caufield, C.6    Chang, G.7    Hendrickson, T.8    Still, W.C.9
  • 29
    • 0043273331 scopus 로고    scopus 로고
    • note
    • int of 0.09 (after absorption correction), limits the crystallographic R-factor to 0.18 for this structure. Nevertheless, the relative stereochemical assignment of interest here is unambiguous.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.