Synthetic Study of Agarofuran-Type Sesquiterpenoid

Abstract

4-Hydroxy zinowol, isolated from the plant Zinowiewia Constaricensis, is an agarofuran-type sesquiterpenoid and known to have reversing activity toward human multidrug resistance NIH-3T3 cells. The structure is characterized by highly oxygenated trans-decalin containing three contiguous quaternary carbon centers. The structural complexity and important biological activity motivated us to start synthetic study of 4-hydroxy zinowol. Herein we report successful construction of the core skeleton of 4-hydroxy zionowol in an enantiomerically pure form by using the asymmetric 1,4-addition, the oxidative dearomatization, and the Diels-Alder reaction as key reactions.