Total Synthesis of (+)-Raistrickindole A

A total synthesis of the indole diketopiperazine alkaloid (+)-raistrickindole A has been completed. The synthesis employs a stereochemical relay strategy wherein an intermolecular nitroso Diels-Alder cycloaddition regio- and diastereoselectively delivers a 3,4-dihydro-1,2-oxazine core, which, in turn, enables a subsequent stereoselective Mukaiyama hydration.