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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthetic Study Aiming at the Tricyclic Core of 12-epi-JBIR-23/24
Yi Man1, Chengying Zhou1, Shaomin Fu1
1Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
Abstract:
The synthetic study toward highly enantio- and diastereoselective synthesis of the tricyclic framework of 12-epi-JBIR-23/24, a natural product analogue showing inhibitory activity against four malignant pleural mesothelioma cell lines, is presented herein. In this synthesis, a rhodium-catalyzed asymmetric three-component Michael/aldol reaction introduces three consecutive tertiary carbon centers, while the unique epoxyquinol core motif is successfully forged via [3,3]-sigmatropic rearrangement of an allylic xanthate, vinylogous Pummerer rearrangement, and a selective mesylation/epoxidation cascade of a triol.
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