Total Synthesis of (±)-Furanether A

Org Lett. 2021 Nov 19;23(22):8843-8846. doi: 10.1021/acs.orglett.1c03353. Epub 2021 Nov 3.

Abstract

The first total synthesis of (±)-furanether A, which exhibits good antifeedant activity, has been concisely achieved in 13 linear steps. Notably, the key rigid tetracyclic skeleton containing a 1-methyl-8-oxabicyclo[3.2.1]octane moiety with two vicinal quaternary carbon centers was rapidly constructed in one step through a unique tandem C-H oxidation/oxa-[3,3] Cope rearrangement/aldol cyclization sequence.

Publication types

  • Research Support, Non-U.S. Gov't