First asymmetric total synthesis of (+)-curcutetraol

Abstract

The first asymmetric total synthesis of (+)-curcutetraol, a marine phenolic bisabolane-type sesquiterpene, was achieved in eight steps in ca. 50% overall yield. The chiral tertiary benzylic alcohol moiety in the o-position of a phenol was constructed in high optical yield (99% ee) by an asymmetric synthesis using a chiral aminal, (2 R,5 S)-2-methoxycarbonyl-3-phenyl-1,3-diazabicyclo[3.3.0]octane.