Step-economical synthesis of the marine ascidian antibiotics cadiolide A, B, and D

J Org Chem. 2015 Jan 2;80(1):681-4. doi: 10.1021/jo502503w. Epub 2014 Dec 8.

Abstract

A concise, modular and efficient synthesis of the title natural products is reported. Prominent steps include (i) one-pot assembly of a key β-aryl-α-benzoylbutenolide building block by regiocontrolled "click-unclick" oxazole-ynone Diels-Alder cycloaddition/cycloreversion and ensuing 2-alkoxyfuran hydrolysis and (ii) a protecting group-free vinylogous Knoevenagel condensation enabling rapid access to cadiolides A, B, and D from a common precursor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis
  • 4-Butyrolactone / chemistry
  • Animals
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Aquatic Organisms / chemistry
  • Cyclization
  • Molecular Structure
  • Urochordata / chemistry*

Substances

  • Anti-Bacterial Agents
  • cadiolide A
  • cadiolide B
  • cadiolide D
  • 4-Butyrolactone