Total Synthesis of (-)-L-755,807: Establishment of Relative and Absolute Configurations

Org Lett. 2016 Apr 15;18(8):1920-3. doi: 10.1021/acs.orglett.6b00758. Epub 2016 Apr 6.

Abstract

The first total synthesis of (-)-L-755,807 and its three stereoisomers was achieved by our Horner-Wadsworth-Emmons reaction for stereoselective formation of trisubstituted olefins, highly diastereoselective Darzens condensation to construct the epoxy-γ-lactam ring, and late-stage coupling of the ring and side-chain segments for efficient convergent synthesis. This synthesis shows that the originally proposed structure of natural (-)-L-755,807 was incorrect and establishes its relative and absolute configurations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Epoxy Compounds / chemical synthesis*
  • Epoxy Compounds / chemistry
  • Lactams / chemical synthesis*
  • Lactams / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alkenes
  • Epoxy Compounds
  • L-755,807
  • Lactams