A Concise, Gram-Scale Total Synthesis of Protectin DX and Related Labeled Versions via a Key Stereoselective Reduction of Enediyne

J Org Chem. 2023 Jun 2;88(11):7088-7095. doi: 10.1021/acs.joc.3c00360. Epub 2023 May 12.

Abstract

We report a gram-scale total synthesis of protectin DX (PDX) following a convergent synthetic route (24 steps) from l-malic acid. This novel synthetic strategy is based on the assembly of three main building blocks using a Sonogashira coupling reaction (blocks A and B) and Wittig olefination (block C) to provide the 22-carbon backbone of PDX. A key stereoselective reduction of enediyne leads to a central E,Z,E-trienic system of PDX and also gives access to its labeled versions (D and T).