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Communication | Special issue | Vol 97, No. 1, 2018, pp.158-162
Published online, 23rd January, 2018
DOI: 10.3987/COM-17-S(T)10
Synthesis of 6/6/6-Tricyclic Ether System via Achmatowicz and Intramolecular Oxa-Michael Reactions

Hiroki Yamamoto, Kohei Torikai, Makoto Ebine, and Tohru Oishi*

*Department of Chemistry, Faculty and Graduate School of Science, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan


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.