Abstract
The trimethylsilyl enol ethers of 1-acetylcyclohexenes 1~ undergo a Lewis acid assisted two fold Michael reactions with Michael acceptors 2~ to produce 5-substituted 2-decalones 3~. The application of these reactions have enabled syntheses of (±)-ε-cadinene 4~ (±)-khusitone 5~ and (±)-khusilal 6~ By employing 8-phenylmenthyl acrylate, optically active 2-decalone 3~ (ca. 70% ee) has been obtained.
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© 1989 Kluwer Academic Publishers
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Hagiwara, H., Okano, A., Akama, T., Uda, H. (1989). Lewis Acid Promoted Sequential Multifold Michael Reactions and Application to Syntheses of Terpenoids. In: Schinzer, D. (eds) Selectivities in Lewis Acid Promoted Reactions. NATO ASI Series, vol 289. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-2464-2_20
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DOI: https://doi.org/10.1007/978-94-009-2464-2_20
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-010-7611-1
Online ISBN: 978-94-009-2464-2
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