Synthesis of 6/6/6-tricyclic ether system via Achmatowicz and intramolecular oxa-michael reactions

Hiroki Yamamoto, Kohei Torikai, Makoto Ebine, Tohru Oishi

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Synthesis of 6/6/6-tricyclic ethers possessing 1,3-diaxial methyl groups was examined via Achmatowicz reaction and intramolecular oxa-Michael reaction. A key precursor was prepared via coupling of an aldehyde with a furyllithium derivative followed by radical deoxygenation of the resulting secondary alcohol. The intramolecular oxa-Michael reaction proceeded in a stereoselective manner to afford cis-fused product as a single isomer.

Original languageEnglish
Pages (from-to)158-162
Number of pages5
JournalHeterocycles
Volume97
Issue number1
DOIs
Publication statusPublished - Jan 1 2018

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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