Concise total synthesis of (+/-)-salinosporamide A, (+/-)-cinnabaramide A, and derivatives via a bis-cyclization process: implications for a biosynthetic pathway? Academic Article uri icon

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.

published proceedings

  • Org Lett

altmetric score

  • 6

author list (cited authors)

  • Ma, G., Nguyen, H., & Romo, D.

citation count

  • 126

complete list of authors

  • Ma, Gil||Nguyen, Henry||Romo, Daniel

publication date

  • May 2007