Total synthesis of valeriananoids A, B, and C via autocatalytic diastereoselective domino Michael reaction |
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| Authors: | Masakazu Fukushima Takashi Hoshi Hisahiro Hagiwara |
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| Affiliation: | a Graduate School of Science and Technology, Niigata University, 8050, 2-Nocho, Ikarashi, Niigata 950-2181, Japan
b Faculty of Engineering, Niigata University, 8050, 2-Nocho, Ikarashi, Niigata 950-2181, Japan |
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| Abstract: | 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. |
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| Keywords: | Bicyclic aliphatic compounds Tricyclic aliphatic compounds Domino Michael reactions Sesquiterpenoid Valeriananoid |
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