Rh-Catalyzed [2 + 2 + 2] Cycloadditions with Benzoquinones: De Novo Access to Naphthoquinones for Lignan and Type II Polyketide Synthesis

The first examples of Rh-catalyzed [2 + 2 + 2] cycloadditions between diynes and benzoquinones are described. The method enables de novo and step-economical access to challenging naphthoquinones that are of relevance to lignan and type II polyketide synthesis. The value of the chemistry is demonstra...

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Bibliographic Details
Published in:Organic letters 2020-01, Vol.22 (1), p.265-269
Main Authors: Wood, James M, da Silva Júnior, Eufrânio N, Bower, John F
Format: Article
Language:English
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Summary:The first examples of Rh-catalyzed [2 + 2 + 2] cycloadditions between diynes and benzoquinones are described. The method enables de novo and step-economical access to challenging naphthoquinones that are of relevance to lignan and type II polyketide synthesis. The value of the chemistry is demonstrated by a short total synthesis of justicidone.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b04266