Total Synthesis of (-)-Salinosporamide A Via a Late Stage C-H Insertion

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2019 Mar 20

PMID 30887693

Citations 4

Authors

Hadi Gholami

Aman Kulshrestha

Olivia K Favor

Richard J Staples

Babak Borhan

Affiliations

Soon will be listed here.

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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