Complete details of an asymmetric synthesis of apicularen (1) are described. The synthesis has been accomplished using a highly diastereo- and enantioselective [4 + 2] annulation for the assembly of the functionalized pyran core. An underdeveloped lactonization method involving an NaH promoted transesterification of an advanced intermediate bearing an aryl cyanomethyl ester was used for the macrolactonization step.