Synthesis of (-)-gloeosporone, a fungal autoinhibitor of spore germination using a pi-allyltricarbonyliron lactone complex as a templating architecture for 1,7-diol construction

Abstract

The synthesis of the germination self-inhibitor (-)-Gloeosporone is reported. The embedded 1,7-diol motif in the product is constructed by an ironcarbonyl tether controlled Mukaiyama aldol reaction. The key step in the synthesis is the reductive removal of the ligating iron species by treatment of an acetoxycomplex 6 with lithium naphthalenide.