Synthesis of (S)-ktedonoketone

Sayaka Ishii, Katsuya Saito, Shigefumi Kuwahara, Masaru Enomoto

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The first total synthesis of (S)-ktedonoketone has been accomplished in 16% overall yield from (R)-2-hydroxybutyric acid by an eight-step sequence that features a highly diastereoselective methallylation of a chiral dioxolanone and a nucleophilic addition of α-lithiostyrene to a Weinreb's amide intermediate followed by ring-closing metathesis of the resulting enone to construct an α,β-disubstituted cyclopentenone ring system. The sign of specific rotation of synthetic (S)-ktedonoketone was opposite to that reported for the natural product.

Original languageEnglish
Article number151915
JournalTetrahedron Letters
Volume61
Issue number22
DOIs
Publication statusPublished - 2020 May 28

Keywords

  • Asymmetric methallylation
  • Ktedonobacteria
  • Ktedonoketone
  • Ring-closing metathesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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