Expedient and Diastereodivergent Assembly of Terpenoid Decalin Subunits having Quaternary Stereocenters through Organocatalytic Robinson Annulation of Nazarov Reagent |
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| Authors: | Barbara Berkes Kristóf Ozsváth Laura Molnár Tamás Gáti Tamás Holczbauer György Kardos Tibor Soós |
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| Affiliation: | 1. Institute of Organic Chemistry, Hungarian Academy of Sciences, Budapest, P.O. Box 286, Hungary;2. Servier Research Institute of Medicinal Chemistry, Budapest, Hungary |
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| Abstract: | We report an expedient approach to highly functionalized cis‐ and trans‐decalines that could function as key structural subunits toward the synthesis of various classes of terpenoids. Key to the strategy is an organocatalyzed Robinson annulation reaction of the Nazarov reagent that affords chiral enone building blocks with high enantioselectivities. The quaternary carbon stereogenic center can direct the subsequent reactions and allow the rapid and diastereoconvergent assembly of complex decalines with contiguous stereocenters. |
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| Keywords: | asymmetric synthesis diastereoselectivity fused-ring systems organocatalysis terpenoids |
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