Synthesis of the Tricyclic Picrotoxane Motif by an Oxidative Cascade Cyclization

Jingming Cao, Waygen Thor, Shenkun Yang, Mengxun Zhang, Wenli Bao, Lizhi Zhu, Wei Yang*, Yuen Kit CHENG, Chi Sing LEE

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4896-4899
Number of pages4
JournalOrganic Letters
Volume21
Issue number12
DOIs
Publication statusPublished - 21 Jun 2019

Scopus Subject Areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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