Synthesis of Xanthanolides including new acylations and their synthetic applications

Mitsuru Shindo, Kenji Matsumoto

Research output: Contribution to journalArticle

Abstract

Xanthanolides were synthesized with intramolecular acylation of organolithium forming a sevenmembered carbocycle and one-pot acylation-Wittig lactonization as key steps. The Cu(II) complex efficiently catalyzed the acylation of thioester in Wittig lactonization under neutral conditions. Using the Cu(II) catalyst, symmetric dithiomalonates were converted into dissymmetric S,O-malonates via selective monoacylation. The key step in this reaction was the thermal formation of an acylketene, the stability of which would contribute to selectivity.

Original languageEnglish
Pages (from-to)1152-1162
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume71
Issue number11
DOIs
Publication statusPublished - Dec 1 2013

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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