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Total Synthesis of (-)-Salinosporamide?A via a Late Stage C-H Insertion.

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.

SUBMITTER: Gholami H 

PROVIDER: S-EPMC6715302 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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

Gholami Hadi H   Kulshrestha Aman A   Favor Olivia K OK   Staples Richard J RJ   Borhan Babak B  

Angewandte Chemie (International ed. in English) 20190410 30

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. ...[more]

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