Add time:08/30/2019 Source:sciencedirect.com
The isolation and characterisation of methyl piperitol, (+)-epieudesmin and (+)-episesamin from the stem bark of Zanthoxylum acanthapodium is reported. The 1H and 13C NMR spectra are correlated with those of other known lignans and it is shown that 13C NMR shifts can be used to assign unambiguously the nature and configuration of the aryl groups in unsymmetrically substituted 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes. Other less satisfactory methods which have in the past been used for this purpose are discussed and in particular the use of coupling constants to assign stereochemistry in this series is strongly criticised. Revised structures for pulviatilol, methyl pluviatilol (fargesin) and xanthoxylol (cas 111407-29-5) are proposed.
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