Total Synthesis of (-)-Bicubebin A, B, (+)-Bicubebin C and Structural Reassignment of (-)-cis-Cubebin

Org Lett. 2017 Oct 6;19(19):5368-5371. doi: 10.1021/acs.orglett.7b02644. Epub 2017 Sep 13.

Abstract

The first total synthesis of (-)-bicubebin A, and two previously unreported dilignans, (-)-bicubebin B and (+)-bicubebin C has been achieved through the dimerization of (-)-cubebin, confirming the structure and absolute stereochemistry of (-)-bicubebin A. Analysis of the data for (-)-bicubebin B showed it matched that of reported compound (-)-cis-cubebin. The NMR data of the subsequently synthesized proposed structure of cis-cubebin confirmed that its original proposed structure was incorrect.

Publication types

  • Research Support, Non-U.S. Gov't