Kenan, Caudill, Venable, and Murray Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United States.
Org Lett. 2010 Nov 5;12(21):5028-31. doi: 10.1021/ol102169w.
The total synthesis of the originally proposed structure of briarellin J is reported in 15 steps from a known compound and in 23 steps from readily available materials. Key reactions include an exo-selective intramolecular Diels-Alder and a substrate-controlled hydroboration. Discrepancies in the spectroscopic data of the synthetic and natural material led to a revision of the assigned structure.
本文报道了从一种已知化合物出发，经过 15 步反应，以及从易得的原料出发，经过 23 步反应，总合成了最初提出的 briarellin J 的结构。关键反应包括一个外选择性的分子内 Diels-Alder 反应和一个底物控制的硼氢化反应。天然产物和合成产物的光谱数据的差异导致了对其结构的修正。
