Development of a Cross-Conjugated Vinylogous [4+2] Anionic Annulation and Application to the Total Synthesis of Natural Antibiotic (±)-ABX

Angew Chem Int Ed Engl. 2020 Apr 16;59(16):6540-6545. doi: 10.1002/anie.201914657. Epub 2020 Feb 25.

Abstract

The cross-conjugated vinylogous [4+2] anionic annulation has been newly developed, the cascade process of which has a high preference for regiochemical control and chemoselectivity, giving rise to exclusively Michael-type adducts in moderate to high yields (up to 94 %, 35 examples). By making use of this approach as a key operation, the first total synthesis of natural antibiotic ABX, in racemic form, has been successfully achieved in a concise 7-step sequence with an overall yield of about 20 %.

Keywords: acceptor; anionic annulation; benzylogous; donor; vinylogous.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anions / chemistry
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Biological Products / chemical synthesis
  • Biological Products / chemistry*
  • Cycloaddition Reaction
  • Stereoisomerism

Substances

  • Anions
  • Anti-Bacterial Agents
  • Biological Products