布瑞来醇 J 的结构的全合成。
Total synthesis of the proposed structure of briarellin J.
机构信息
Kenan, Caudill, Venable, and Murray Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United States.
出版信息
Org Lett. 2010 Nov 5;12(21):5028-31. doi: 10.1021/ol102169w.
Abstract
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.
摘要
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。
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