Organic Letters
Organic Letters
5 years ago

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

Total Synthesis of (−)-Bicubebin A, B, (+)-Bicubebin C and Structural Reassignment of (−)-cis-Cubebin
Samuel J. Davidson, Brent R. Copp, David Barker, A. Norrie Pearce
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02644

DOI: 10.1021/acs.orglett.7b02644

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