Work

Total Synthesis of (−)‐Salinosporamide A via a Late Stage C−H Insertion

Year: 2019

Type: article

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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201900340

Authors: Hadi Gholami, Aman Kulshrestha, Olivia K. Favor, Richard J. Staples, Babak Borhan

Institution: Michigan State University

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green