Katcher Matthew, Jamison Timothy F
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, MA 02139 USA.
Tetrahedron. 2018 Mar 15;74(11):1111-1122. doi: 10.1016/j.tet.2018.01.039. Epub 2018 Feb 2.
Shortly after the initial isolation of marine ladder polyether natural products, biomimetic epoxide-opening cascade reactions were proposed as an efficient strategy for the synthesis of these compounds. However, difficulties in assembling the cascade precursors have limited the realization of these cascades. In this report, we describe strategies that provide convergent access to cascade precursors via regioselective allylation and efficient fragment coupling. We then investigate epoxide-opening cascades promoted by strong bases for the formation of fused tetrahydropyrans. These strategies are evaluated in the context of the synthesis of rings CDEFG of brevisulcenal F.
在首次分离出海生梯状聚醚天然产物后不久，仿生环氧开环级联反应就被提出作为合成这些化合物的有效策略。然而，级联前体的组装困难限制了这些级联反应的实现。在本报告中，我们描述了通过区域选择性烯丙基化和高效片段偶联来收敛合成级联前体的策略。然后，我们研究了强碱促进的环氧开环级联反应以形成稠合四氢吡喃。这些策略在短裸壳霉烯醛F的CDEFG环合成背景下进行了评估。
