A deconstruction–reconstruction strategy to access 1-naphthol derivatives: application to the synthesis of aristolactam scaffolds

Literature Information

Publication Date 2023-10-27
DOI 10.1039/D3OB01603J
Impact Factor 3.876
Authors

Jeong Min Bak, Moonyeong Song, Inji Shin, Hee Nam Lim


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Abstract

A deconstruction–reconstruction strategy for the synthesis of multisubstituted polycyclic aromatic hydrocarbons (PAHs) is delineated herein. The deconstruction step enables the synthesis of o-cyanomethylaroyl fluorides that are bifunctional substrates holding both a pro-nucleophile and an electrophile. The construction step involves a formal [4 + 2] benzannulation using o-cyanomethylaroyl fluorides and active methylenes. The utility of this synthetic method is also demonstrated by the synthesis of a tetracyclic aristolactam derivative.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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