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Article Abstract
We report an enantiodivergent total synthesis of β-lycorane, accomplished in three steps, achieving an overall yield of 28% and an atom economy of 78% via cycloaddition catalyzed by a chiral -2,5-disubstituted pyrrolidine organocatalyst. Following successful reaction optimization, a broad substrate scope was explored, affording the corresponding cycloadducts in up to 80% yield, 15:1 dr, and 94% ee. This scalable methodology is also compatible with the branched 2,4-dienals. Importantly, the 5-substituent on the organocatalyst plays a pivotal role in controlling the regioselectivity, effectively suppressing the undesired α- and γ-reactivity.
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Concise, Atom-Economical, and Enantiodivergent Total Synthesis of β-Lycorane via Organocatalyzed [4+2] Cycloaddition Reaction.
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Article Synopsis
- - A new nickel-catalyzed method was developed to create the final two rings of the complex molecule linoxepin using a β-bromo acetal and dibenzoxepin.
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