A Unified Modular Synthetic Strategy for Dictyodendrins F, H, I, and G

Org Lett. 2017 Sep 15;19(18):4996-4999. doi: 10.1021/acs.orglett.7b02511. Epub 2017 Aug 28.

Abstract

A unified modular synthetic strategy has been developed for the first total synthesis of dictyodendrins G and synthesis of dictyodendrin F, H and I in 11 steps. The synthesis features consecutive functionalization of the core aminoquinone by palladium-mediated Suzuki-Miyaura coupling reaction, 1,4-addition, acylation and base mediated formation of a pyrrolinone, and the formation of carbazolequinone moiety through a formal [3 + 2] cycloaddition using arynes generated in situ. Several dictyodendrin analogues were also synthesized using this strategy.

Publication types

  • Research Support, Non-U.S. Gov't