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Total Synthesis of (-)-Salinosporamide A via a Late Stage C-H Insertion
Hadi Gholami1, Aman Kulshrestha1, Olivia K Favor1
1Department of Chemistry, Michigan State University, E. Lansing, MI, 48824, USA.
Abstract:
The synthesis of (-)-salinosporamide A, a proteasome inhibitor, is described. The synthesis highlights the assembly of a densely decorated pyrrolidinone core via an aza-Payne/hydroamination sequence. Central to the success of the synthesis is a late-stage C-H insertion reaction to functionalize a sterically encumbered secondary carbon. The latter functionalization leads to an enabling transformation where most of the prototypical strategies failed.
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