Convergent synthesis of trans-fused 6/n/6/6 (n=7, 8) tetracyclic ether system via α-cyano ethers

Tohru Oishi, Koji Watanabe, Michio Murata

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34 Citations (Scopus)

Abstract

A convergent method for synthesizing 6/n/6/6 (n=7, 8) tetracyclic ether system via two-rings construction of the central n/6 ring system was developed. The key steps of the present synthesis involve a ring-closing metathesis reaction for the construction of the seven- and eight-membered rings, and reductive etherification for the tetrahydropyrans. Unification of the two fragments through acetal formation, followed by regioselective cleavage of the acetal using TMSCN/TMSOTf in the presence of 2,6-di-tert-butyl-4-methylpyridine, afforded the α-cyano ether, of which the nitrile group was manipulated to give the precursors of the ring-closing reactions.

Original languageEnglish
Pages (from-to)7315-7319
Number of pages5
JournalTetrahedron Letters
Volume44
Issue number39
DOIs
Publication statusPublished - Sep 22 2003
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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