Unified Total Synthesis of Hetiamacins A–D

Shogo Tsukaguchi, Masaru Enomoto, Ryo Towada, Yusuke Ogura, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

A concise enantioselective total synthesis of hetiamacin A has been accomplished from a known l-aspartic acid derivative by an eight-step sequence that features ammonolytic opening of the γ-lactone moiety of amicoumacin C followed by 1,3-oxazinane ring formation in one pot. Hetiamacins B–D with putatively assigned stereochemistries have also been synthesized from amicoumacin C, each in three steps involving tetrahydro-4(1H)-pyrimidinone ring formation. The excellent NMR spectroscopic agreement of the synthetic materials with the corresponding natural products, coupled with biosynthetic considerations, has enabled the full stereochemical assignments of hetiamacins B–D.

Original languageEnglish
Pages (from-to)6110-6116
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number35
DOIs
Publication statusPublished - 2019 Sep 22

Keywords

  • Alkaloids
  • Hetiamacin
  • Natural products
  • Nitrogen heterocycles
  • Total synthesis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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