Total Synthesis of Gymnocin-A

J Am Chem Soc. 2015 Nov 18;137(45):14513-6. doi: 10.1021/jacs.5b10082. Epub 2015 Nov 10.

Abstract

A convergent total synthesis of cytotoxic marine natural polycyclic ether, gymnocin-A (1), is described. The synthesis features three iterations of an oxiranyl anion strategy, involving base-mediated cycloetherification, ring expansion, and reductive etherification, for the construction of the FGH fragment and for its coupling with the ABC and KLMN fragments.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ethers, Cyclic / chemical synthesis*
  • Ethers, Cyclic / chemistry
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Ethers, Cyclic
  • gymnocin A