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Org Lett. 2018 Nov 2;20(21):6701-6704. doi: 10.1021/acs.orglett.8b02779. Epub 2018 Oct 22.

Asymmetric Synthesis of an Advanced Tetracyclic Framework of (+)-Sarain A.

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1
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy , Sichuan University , Chengdu 610041 , China.

Abstract

An asymmetric synthetic approach to a tetracyclic framework of the marine-derived alkaloid (+)-sarain A has been developed. The key steps to constructing the congested diazatricycloundecane core include an asymmetric Diels-Alder cycloaddition, an Ireland-Claisen rearrangement, and an intramolecular aziridination/ring-opening sequence.

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