Stereoselective total synthesis of amicoumacin C

Tomomi Suzuki, Tomohiro Nagasawa, Masaru Enomoto, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

The enantio- and diastereoselective total synthesis of amicoumacin C was achieved from l-phenylalanine in 17% overall yield through 13 steps via condensation between an amine and an acid segment. The amine segment was prepared from l-leucine in 42% yield by a 7-step sequence involving a diastereoselective reduction of an α-dibenzylamino ketone intermediate, while the acid segment was obtained from l-phenylalanine by using acidic hydrolysis of an acetonide-protected amide accompanied by concomitant lactonization as a key step.

Original languageEnglish
Pages (from-to)1992-1997
Number of pages6
JournalTetrahedron
Volume71
Issue number13
DOIs
Publication statusPublished - 2015 Apr 1

Keywords

  • Amicoumacin
  • Antibacterial
  • Diastereoselective reduction
  • Isocoumarin
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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