Total Synthesis of epi-Trichosetin

J Org Chem. 2018 Dec 21;83(24):15170-15177. doi: 10.1021/acs.joc.8b02450. Epub 2018 Dec 3.

Abstract

The natural 3-decalinoyltetramic acid epi-trichosetin was synthesized in ten steps starting from ( R)-(+)-citronellal using an intramolecular Diels-Alder reaction and a Lacey-Dieckmann cyclization as the key steps. The use of a 2-nitrobenzyl protecting group resulted in an efficient synthetic endgame. The natural product was obtained in 4.1% overall yield.

Publication types

  • Research Support, Non-U.S. Gov't