Examination of Diels-Alder/Tsuji-Trost Route towards Kopsia Alkaloids

Ekaterina A. Zhigileva, Marina V. Molchanova, Pavel N. Solyev, Alexander A. Korlyukov, Mikhail S. Baranov, Andrey A. Mikhaylov*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A reaction sequence of Diels Alder cycloaddition and Tsuji-Trost allylation was examined in terms of its application to the synthesis of kopsinine and the related Kopsia alkaloids. Results of the studies in two synthetic directions are presented herein: 1) synthesis of the properly substituted diene, required for the Diels Alder step; and 2) model studies and optimization of the key reaction sequence in the absence of side-chain. Details on the challenging introduction of the side-chain into tetrahydrocarboline ketone and its silylation, resulting in rare but unproductive vinylogous Claisen cyclization, and the successful Mannich/ Mukaiyama aldol sequence are disclosed in the first direction. In the second direction, the endo-selective Diels Alder reaction with allyl acrylate and Tsuji Trost allylation providing incorrect stereochemistry are disclosed. Interaction of both dienes with an alkyne provides carbazoles via Alder Rickert reaction.

Original languageEnglish
Pages (from-to)346-356
Number of pages11
JournalSynthesis
Volume56
Issue number2
DOIs
Publication statusPublished - 4 Sept 2023
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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