Synthesis of the Tricyclic Picrotoxane Motif by an Oxidative Cascade Cyclization
Synthesis of the Tricyclic Picrotoxane Motif by an Oxidative Cascade Cyclization
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通过氧化级联环化合成三环吡咯烷基序
DOI：
10.1021/acs.orglett.9b01806
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发表时间：
2019-06-21
期刊：
影响因子：
5.2
通讯作者：
Lee, Chi-Sing
中科院分区：
文献类型：
--
作者：
Cao, Jingming;Thor, Waygen;Lee, Chi-Sing
已开发的氧化级联环化的β-酮酯的三环picrotoxane基序的建设在一个单一的步骤，和DFT计算建议一个可能的阳离子环化机制。该级联环化可以在20 g规模下操作以获得77%总收率的三环产物，其进而可以转化为多用途中间体，用于进一步加工为苦氧烷及其结构相关的化合物。
An oxidative cascade cyclization of beta-keto esters has been developed for the construction of the tricyclic picrotoxane motif in a single step, and DFT calculations suggested a possible cationic cyclization mechanism. This cascade cyclization can be operated on a 20 g scale to obtain a 77% total yield of the tricyclic products, which in turn can be converted to versatile intermediates for further elaboration to picrotoxanes and their structurally related compounds.