Total Synthesis of Amphirionin-4

Org Lett. 2016 May 20;18(10):2399-402. doi: 10.1021/acs.orglett.6b00883. Epub 2016 Apr 12.

Abstract

An expeditious enantioselective total synthesis of amphirionin-4, a remarkably potent promoter of the proliferation of ST-2 cells, has been achieved from (±)-(E)-1,4-hexadien-3-ol by an 8-pot sequence that features the Sharpless kinetic resolution, iodoetherification, and the CBS reduction to install the stereocenters, utilization of four one-pot transformations to streamline the synthetic process, and the Stille coupling reaction at nearly the center of the target molecule to complete the total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't