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The Catalytic Enantioselective, Protecting Group-Free Total Synthesis of (+)-Dichroanone

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posted on 2006-06-21, 00:00 authored by Ryan M. McFadden, Brian M. Stoltz
Herein we report the first enantioselective total synthesis of (+)-dichroanone, confirming the absolute configuration of the natural product. This protecting group-free route features the first application of our enantioselective Tsuji allylation in the context of a natural product total synthesis. Additionally, this 11-step preparation of the molecule from commercial material features a novel Kumada-aromatization strategy and a rapid sequence for the conversion of a phenol to a hydroxy-p-benzoquinone.