State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.
J Org Chem. 2012 May 4;77(9):4217-25. doi: 10.1021/jo300556r. Epub 2012 Apr 18.
We present in this report the development of a convergent and highly stereocontrolled cycloaddition strategy toward the synthesis of C-1, C-6, and C-14 tris-oxygenated eudesmane sesquiterpenoids. This approach was demonstrated in the first total synthesis of (±)-6β,14-epoxyeudesm-4(15)-en-1β-ol (1), a structurally unique ethereal eudesmane sesquiterpenoid, via an effective Diels-Alder construction of a compact functionalized tricycle intermediate from readily available N-benzylfurfurylamine (2) and homoprenyl maleic anhydride (3) as the C(5) and C(10) building blocks, respectively.
我们在本报告中介绍了一种会聚且高度立体控制的环加成策略的发展，该策略旨在合成 C-1、C-6 和 C-14 三氧代桉烷倍半萜。该方法在（±）-6β，14-环氧桉烷-4（15）-烯-1β-醇（1）的首次全合成中得到了证明，（1）是一种结构独特的醚型桉烷倍半萜，通过有效构建紧凑的功能化三环中间体，从易得的 N-苄基糠基胺（2）和同丙烯基马来酸酐（3）分别作为 C（5）和 C（10）构建块，实现了 Diels-Alder 反应。
