Bioinspired Synthesis of the Furopyrazine Alkaloid Hyrtioseragamine A

J Org Chem. 2021 Mar 19;86(6):4779-4785. doi: 10.1021/acs.joc.1c00174. Epub 2021 Mar 9.

Abstract

A biosynthetic hypothesis proposed herein was used to guide the total synthesis of the marine-derived alkaloid hyrtioseragamine A. In the key biomimetic step, an enedione underwent acid-mediated isomerization-cyclodehydration to form the rare furopyrazine core of the natural product. The spectroscopic data for the synthetic sample is in full agreement with that described in the isolation report.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids*
  • Biological Products*
  • Biomimetics
  • Furans
  • Pyrazines

Substances

  • Alkaloids
  • Biological Products
  • Furans
  • Pyrazines
  • hyrtioseragamine A