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A Bio-Inspired Synthesis of Peshawaraquinone

08 August 2022, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A ten-step bio-inspired enantioselective synthesis of peshawaraquinone, an uncommon and complex naphthoquinone mero-terpenoid is described. Key to the success of this synthetic pathway is a well-tuned HFIP-promoted metal-free allylation was developed to coupling lawsone with allylic alcohols, together with an usual organo-catalyzed [3+2] cycloaddition for con-structing the bicyclo[3.2.1]octane core structure. Further investigation disclosed peshawaraquione is a racemic mixture.

Keywords

total synthesis
biomimetic synthesis

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Version History

Aug 08, 2022 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2022-drjln
D O I: 10.26434/chemrxiv-2022-drjln [opens in a new tab]

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.

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