Scope and applications of second generation palladium-catalyzed cycloalkenylation. Stereoselective total syntheses of isoiridomyrmecin, isodihydronepetalactone, and ¦Á-skytanthine

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• 作者：Kazutaka Takeda ; Masahiro Toyota  ; ;   ; ^{toyota@c.s.osakafu-u.ac.jp}
• 关键词：Second generation palladium-catalyzed cycloalkenylation ; Bicyclo[3.2.1]octanes ; 3-Azabicyclo[3.3.0]octanes ; 3-Azabicyclo[4.3.0]nonanes ; ¦Á-Skytanthine
• 刊名：Tetrahedron
• 出版年：2011
• 出版时间：23 December 2011
• 年：2011
• 卷：67
• 期：51
• 页码：9909-9921
• 全文大小：1261 K

文摘

Functionalized bicyclo[3.2.1]octanes, -oxabicyclo-[4.3.0]nonanes, 3-azabicyclo[3.3.0]octanes, and 3-azabicyclo[4.3.0]nonanes were easily synthesized via a second generation palladium-catalyzed cycloalkenylation. Isoiridomyrmecin and isodihydronepetalactone, both of which feature a 3-oxabicyclo[4.3.0]nonane subunit, were stereoselectively synthesized via a second generation palladium-catalyzed cycloalkenylation as the key step. ¦Á-Skytanthine, a typical 3-azabicyclo[4.3.0]nonane alkaloid, was also constructed using the same catalytic cyclization protocol.