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Published on: February 16, 2018
Synthesis of the Tricyclic Picrotoxane Motif by an Oxidative Cascade Cyclization
Jingming Cao1, Waygen Thor2, Shenkun Yang1
1State Key Laboratory of Chemical Oncogenomics , Peking University Shenzhen Graduate School , Shenzhen University Town, Xili, Shenzhen 518055 , China.
Abstract:
An oxidative cascade cyclization of β-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.
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