Total synthesis of exigurin: the Ugi reaction in a hypothetical biosynthesis of natural products

Org Biomol Chem. 2020 Jan 28;18(4):687-693. doi: 10.1039/c9ob02249j. Epub 2020 Jan 6.

Abstract

The first total synthesis of a marine natural product, exigurin, has been accomplished in 13 steps starting from (+)-menthone. The key intermediate (-)-10-epi-axisonitrile-3 was prepared by stereoselective intramolecular cyclopropanation followed by a cyclopropane ring opening reaction by the azide anion. The bioinspired Ugi reaction of (-)-10-epi-axisonitrile-3, formaldehyde, sarcosine and methanol successfully constructed the target exigurin in which its terpene and amino acid units were linked through an amide bond.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis*
  • Imino Acids / chemical synthesis*
  • Sesquiterpenes / chemical synthesis*
  • Stereoisomerism

Substances

  • Biological Products
  • Imino Acids
  • Sesquiterpenes
  • boneratamide A