Du Qiang, Fan Zhibo, Yang Ming
State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, Gansu Province, 730000, China.
Angew Chem Int Ed Engl. 2024 Apr 22;63(17):e202400956. doi: 10.1002/anie.202400956. Epub 2024 Mar 19.
We have accomplished the first and asymmetric total synthesis of principinol B, a grayanoid possessing an oxabicyclo[3.2.1] architecture. A functionalized 5/7/6/5 tetracyclic intermediate was assembled in a convergent manner by a diastereoselective intermolecular aldol reaction and subsequent carbonyl-olefin metathesis of two enantiomerically enriched fragments. The oxabicyclo[3.2.1] architecture containing a 6,10-ether bridge was constructed by the Williamson ether synthesis.
我们完成了principinol B的首次不对称全合成，principinol B是一种具有氧杂双环[3.2.1]结构的木藜芦烷类化合物。通过非对映选择性分子间羟醛反应和随后两个对映体富集片段的羰基-烯烃复分解反应，以汇聚方式组装了一个官能化的5/7/6/5四环中间体。通过威廉姆森醚合成构建了含有6,10-醚桥的氧杂双环[3.2.1]结构。
