Study for diastereoselective aldol reaction in flow: synthesis of (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid, a key component of cyclodepsipeptide HDAC inhibitors

Takayuki Doi, Hiroyuki Otaka, Koji Umeda, Masahito Yoshida

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

Abstract Flow synthesis of (E)-(S)-3-hydroxy-7-tritylthio-4-heptenoic acid (5), a key component of cyclodepsipeptide histone deacetylase inhibitors was achieved. An efficient flow system for the synthesis of α, β-unsaturated ester 8 was established using a flow reactor column packed with polymer-supported 1,4-diazabicyclo[2.2.2]octane and a fast mixing accessible flow reactor (Comet X-01). Enal 9 was efficiently prepared by a partial reduction of the α, β-unsaturated ester 8 using diisobutylaluminium hydride in the flow system, and the continuous-flow diastereoselective aldol reaction was performed at low temperature, giving a good yield and diastereoselectivity of the desired aldol 10.

Original languageEnglish
Article number26769
Pages (from-to)6463-6470
Number of pages8
JournalTetrahedron
Volume71
Issue number37
DOIs
Publication statusPublished - 2015 Aug 7

Keywords

  • Aldol reaction
  • Cyclodepsipeptide
  • Diastereoselective
  • Flow synthesis
  • Histone deacetylase inhibitor

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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