Total synthesis of valeriananoids A, B, and C via autocatalytic diastereoselective domino Michael reaction

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• 作者：Masakazu Fukushima ; Akihiro Morii ; Takashi Hoshi ; Toshio Suzuki ; Hisahiro Hagiwara
• 关键词：Bicyclic aliphatic compounds ; Tricyclic aliphatic compounds ; Domino Michael reactions ; Sesquiterpenoid ; Valeriananoid
• 刊名：Tetrahedron
• 出版年：2007
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：23 July 2007
• 卷：63
• 期：30
• 页码：7154-7164
• 文件大小：548 K

摘要

Natural enantiomers of unique tricyclic sesquiterpenoids, valeriananoids A–C 1–3, have been synthesized starting from bicyclo[2.2.2]octane-2,5-dione derivative 11, which was obtained by diastereoselective catalytic domino Michael reaction of oxophorone 5 with 8-phenylmenthyl acrylate 10 by LDA or silica-gel-base (NMAP-Li). The tricyclic ring was closed selectively by intramolecular 6-endo-trig mode cyclization of the ketyl radical, which was generated from keto-allylether 25 by either lithium or sodium naphthalenide.