The Total Synthesis of Raistrickindole A.

The total synthesis of raistrickindole A has been achieved, thereby confirming the proposed structure as an N -hydroxylated DKP. In the first but less selective approach, the DKP was built up by cyclization of a diastereoisomerically mixed N -hydroxylated dipeptide. In the second approach, the same DKP was constructed stereoselectively by the intramolecular Mitsunobu reaction of a hydroxamic acid. The synthesis was completed by a stereoselective oxidative cyclization.