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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Divergent synthesis of trans-fused polycyclic ethers by a convergent oxiranyl anion strategy
Takeo Sakai1, Ai Sugimoto, Hiroki Tatematsu
1Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku-ku, Nagoya 468-8503, Japan.
Abstract:
Octacyclic polyethers that correspond to the CDEFGHIJ-ring system of yessotoxin as well as G- and/or I-ring-modified analogues were synthesized in a divergent manner, starting from a common intermediate, using an [X + 2 + Y]-type convergent method. Reaction of a triflate with the oxiranyl anion generated from an epoxy sulfone, followed by ring expansion, allowed for the incorporation of medium-sized ring ethers into the key intermediate. Subsequent acetal formation and reductive etherification afforded various octacycles containing seven- and eight-membered ether rings.
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