부산대학교 도서관

Akaterpin, a specific inhibitor of PI-specific PLC, consists of two decalin rings and a hydroquinone disulfate moiety. Relative stereochemistry of each decalin moiety was determined dependently, and, therefore, relative structure has not been yet determined. Our strategy to akaterpin was to construct the upper decalin first, and construct the lower dacalin by intramolecular Diels-Alder reaction. The resulting two isomers were separated, and each isomer was transformed to the target molecule. We found that the H-NMR spectrum of the target molecule (racemic) derived from the major isomer of Diels-Alder reaction was found to be identical to that of natural akaterpin. Thus, we were able to achieve a total synthesis of akaterpin (racemic) and determine the relative stereochemistry.