Stereo- and substituent-enabled divergent synthesis of 5,6-spiroketal analogs of avermectin containing a triazole function

Takeshi Yamada, Yuki Horimatsu, Tomoyasu Hirose, Akihiro Sugawara, Satoshi Ōmura, Toshiaki Sunazuka

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Stereo-divergent construction of a 5,6-spiroketal moiety, together with an efficient strategy to access various avermectin analogs containing a triazole group, has been accomplished. In the spirocyclization event, a C21R spiroketal product was selectively obtained using Zn(OTf)2 as a Lewis acid. Conversely, use of Sc(OTf)3 afforded a C21S spiroketal compound as the major product. One pot triazole formation between three TMS-alkyne substrates and organic azides effectively provided the corresponding anti-triazole products. This strategy generates stereochemical and substituent diversity among avermectin analogs. Some of the 5,6-spiroketal analogs showed anti-nematodal activity comparable to ivermectin.

Original languageEnglish
Pages (from-to)3119-3124
Number of pages6
JournalTetrahedron Letters
Volume58
Issue number32
DOIs
Publication statusPublished - 2017
Externally publishedYes

Keywords

  • Anthelmintic drug
  • Click chemistry
  • Diversity
  • Ivermectin
  • Spiroketal

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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