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

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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

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Ethers
Aldehydes
Isomers
Ether
Alcohols
Derivatives

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Synthesis of 6/6/6-tricyclic ether system via Achmatowicz and intramolecular oxa-michael reactions. / Yamamoto, Hiroki; Torikai, Kohei; Ebine, Makoto; Oishi, Tohru.

In: Heterocycles, Vol. 97, No. 1, 01.01.2018, p. 158-162.

Research output: Contribution to journalArticle

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