Total Synthesis of Tedarene A

J Nat Prod. 2017 May 26;80(5):1623-1630. doi: 10.1021/acs.jnatprod.7b00199. Epub 2017 May 2.

Abstract

Tedarene A is a macrocyclic diaryl ether heptanoid isolated from the marine sponge Tedania ignis showing an inhibitory effect against nitric oxide production. The first total synthesis of tedarene A was achieved starting from the commercially available 3-(4-methoxyphenyl)propan-1-ol in nine steps and 15.3% overall yield. The synthetic sequence featured an E,Z-dienic bond introduction and a macrocyclization under Ullman conditions. During the synthesis, the E,E-isomer of tedarene A was also obtained and fully characterized.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Diarylheptanoids / chemical synthesis*
  • Diarylheptanoids / chemistry
  • Diarylheptanoids / isolation & purification*
  • Ethers / chemistry*
  • Molecular Structure
  • Porifera / chemistry*
  • Propanols / chemical synthesis*
  • Propanols / chemistry
  • Stereoisomerism

Substances

  • 3-(4-methoxyphenyl)propan-1-ol
  • Diarylheptanoids
  • Ethers
  • Propanols
  • tedarene A