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The oxidative coupling of phenol promoted by thallium tris-(trifluoroacetate) has been reported to give macrocyclic biaryl ether in nonspecified yield. See ref 10.
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We thank Professor Nagai for kindly sending us the NMR spectra of natural acerogenin C and aceroside IV.
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One of the reviewers pointed out that hindered rotation of the para-disubstituted aromatic ring cannot be excluded in acerogenin A. The lack of anisochrony can be attributed to the absence of any of the following three effects: (1) hindered rotation of the aromatic ring; (2) hindered interconversion of planary chiral conformations associated with the flipping of the seven-membered chain; (3) the center of chirality at C-12. Note that the second effect interconverts in the case of acerogenin A enantiomers while it does not in the case of acerogenin C diastereomers.
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13C NMR, elemental analysis and HRMS) are in accord with the structural assignment of 43 and 44, the planar chiralities of these two compounds were not thoroughly determined. The physical data described in the Experimental Section were arbitrary assigned for 43 and 44.
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-
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