Abstract
Based on the hemiketal obtained by the carbonyl eneketalization of the Diels-Alder adduct of levoglucosenone and isoprene with acetaldehyde, two methods have been suggested for incorporating the carboxy group of loganin at the pyran ring. The first method involved one-pot conversion employing ozonolytic cleavage of the double bond, ozonide reduction, <em>in situ</em> aldehyde oxidation and esterification. An alternative five-step sequential conversion of the ketal, with isolation and identification of intermediate compounds, involved ketalization, Wagner <em>vic</em>-hydroxylation of the double bond, periodate cleavage of diols, <em>in situ</em> oxidation of the aldehyde to an acid, and esterification.
Published Version
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