Concise Total Synthesis of (+/-)-salinosporamide A, (+/-)-cinnabaramide A, and Derivatives Via a Bis-cyclization Process: Implications for a Biosynthetic Pathway?

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2007 May 5

PMID 17477539

Citations 27

Authors

Gil Ma

Henry Nguyen

Daniel Romo

Affiliations

Soon will be listed here.

Abstract

4-Alkylidene-beta-lactones (hetero ketene dimers) and alpha-amino acids are useful precursors for total syntheses of the beta-lactone-containing proteasome inhibitors salinosporamide A, cinnabaramide A, and derivatives. A key step is a nucleophile-promoted, bis-cyclization of keto acids that simultaneously generates the gamma-lactam and beta-lactone of these natural products. This reaction sequence may have implications for the biosynthesis of these natural products.

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