School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland 1010, New Zealand.
Org Lett. 2017 Oct 6;19(19):5368-5371. doi: 10.1021/acs.orglett.7b02644. Epub 2017 Sep 13.
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.
首次实现了 (-)-bicubebin A 的全合成，以及两种之前未报道的二芳基丁烷类化合物（-)-bicubebin B 和 (+)-bicubebin C，通过（-)-cubebin 的二聚化反应得到，证实了（-)-bicubebin A 的结构和绝对立体化学。对（-)-bicubebin B 的数据分析表明，它与报道的 (-)-cis-cubebin 化合物相匹配。随后合成的 cis-cubebin 的提议结构的 NMR 数据证实了其原始提议结构是不正确的。
