Development of biofunctional molecules based on total synthesis of natural products

Ichiro Hayakawa

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Development of biofunctional molecules is an essential research field in the progress of chemical biology and medicinal chemistry. Natural products show various biological activities, thus they are expected to be lead compounds of novel-type of drugs. Also, natural products with a novel mechanism of action are important tools for study of biological phenomena. We have achieved the total synthesis of (-)-13-oxyingenol. This approach is highlighted by ring-closing olefin metathesis for the construction of an inside-outside framework and Mislow-Evans-type [2,3]-sigmatropic rearrangement for the introduction of a hydroxy group at C5. On the other hand, we have synthesized a hybrid molecule, consisting of the macrolactone part in aplyronine A and the side chain part in mycalolide B, by using two asymmetric Ni/Cr-mediated reaction and an intramolecular Ni/Cr-mediated macrocyclization as the key steps and have biologically evaluated this compound.

Original languageEnglish
Pages (from-to)126-136
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume72
Issue number2
DOIs
Publication statusPublished - 2014
Externally publishedYes

Keywords

  • 13-oxyingenol
  • Aplyronine A
  • Biofunctional molecule
  • Hybrid molecule
  • Natural product
  • Total synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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