Divergent Synthesis of Trans-Fused Polycyclic Ethers by a Convergent Oxiranyl Anion Strategy

详细信息    查看全文

• 作者：Takeo Sakai ; Ai Sugimoto ; Hiroki Tatematsu ; Yuji Mori
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：December 21, 2012
• 年：2012
• 卷：77
• 期：24
• 页码：11177-11191
• 全文大小：688K
• 年卷期：v.77,no.24(December 21, 2012)
• ISSN：1520-6904

文摘

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.