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Org Lett. 2019 Jun 21;21(12):4896-4899. doi: 10.1021/acs.orglett.9b01806. Epub 2019 Jun 12.

Synthesis of the Tricyclic Picrotoxane Motif by an Oxidative Cascade Cyclization.

Author information

1
State Key Laboratory of Chemical Oncogenomics , Peking University Shenzhen Graduate School , Shenzhen University Town, Xili, Shenzhen 518055 , China.
2
Department of Chemistry , Hong Kong Baptist University , Kowloon Tong , Hong Kong SAR , China.
3
Institute of Translational Medicine, Shenzhen Second People's Hospital , The First Affiliated Hospital of Shenzhen University, Health Science Centre , Shenzhen 518035 , China.
4
Institute for Research and Continuing Edition (Shenzhen) , Hong Kong Baptist University , Industrialization Complex Building, Shenzhen Virtual University Park, Shenzhen 518000 , 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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