Bioinspired total synthesis of (?)-gymnothelignan L?

Organic Chemistry Frontiers Pub Date: 2018-01-22 DOI: 10.1039/C8QO00026C

Abstract

The first asymmetric total synthesis of gymnothelignan L has been accomplished in 14 steps with 11.2% overall yield. The synthetic approach features an anti Evans aldol reaction, a diastereoselective methylation, a Suzuki–Miyaura coupling and a bioinspired desymmetric transannular Friedel–Crafts reaction. Notably, the synthesis further demonstrated the biogenetic pathway that dibenzocyclooctene-type lignans are generated from eupomatilone-type lignans.

Graphical abstract: Bioinspired total synthesis of (?)-gymnothelignan L
Recommended Literature