First Asymmetric Total Synthesis of Salinosporamides D and I Using Memory of Chirality and Dynamic Kinetic Resolution

Abstract

AbstractThe first total synthesis of (−)‐salinosporamide D was achieved using d‐serine as the sole chiral source. This approach stands out for its application of the principles of memory of chirality and dynamic kinetic resolution in the intramolecular aldol reaction of serine‐derived oxazolidines. These strategies enabled the rapid construction of a pyrrolidinone core and installation of contiguous stereocenters. The key intermediate was readily obtained, culminating the asymmetric total synthesis of salinosporamide D. The total synthesis of salinosporamides A and I was also achieved using the same chemistry.