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A bioinspired, one-step total synthesis of peshawaraquinone.

ABSTRACT: A concise synthesis of a stereochemically complex meroterpenoid, peshawaraquinone, via the unsymmetrical dimerization of its achiral precursor, dehydro-α-lapachone, is reported. Enabled by reversible oxa-6π-electrocyclizations of 2H-pyran intermediates, the base-catalyzed dimerization sets up an intramolecular (3 + 2) cycloaddition, with the formation of six stereocenters during the cascade. Combining the generation and in situ dimerization of dehydro-α-lapachone allows a one-step total synthesis of peshawaraquinone from lawsone and prenal.

SUBMITTER: Vieira de Castro T 

PROVIDER: S-EPMC9890946 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature

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A bioinspired, one-step total synthesis of peshawaraquinone.

Vieira de Castro Tomás T   Huang David M DM   Sumby Christopher J CJ   Lawrence Andrew L AL   George Jonathan H JH  

Chemical science 20221221 4

A concise synthesis of a stereochemically complex meroterpenoid, peshawaraquinone, <i>via</i> the unsymmetrical dimerization of its achiral precursor, dehydro-α-lapachone, is reported. Enabled by reversible oxa-6π-electrocyclizations of 2<i>H</i>-pyran intermediates, the base-catalyzed dimerization sets up an intramolecular (3 + 2) cycloaddition, with the formation of six stereocenters during the cascade. Combining the generation and <i>in situ</i> dimerization of dehydro-α-lapachone allows a on  ...[more]

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