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Access to Naphthoic Acid Derivatives through an Oxabenzonorbornadiene Rearrangement.

ABSTRACT: Herein, the synthesis of 1-hydroxy-2-naphthoic acid esters through an unexpected Lewis-acid-mediated 1,2-acyl shift of oxabenzonorbornadienes is reported. Using this methodology, novel substitution patterns for 1-hydroxy-2-naphtoic acid esters can be obtained. A mechanistic proposal and rationale for this transformation, the products of which had been previously incorrectly characterized, is given.

SUBMITTER: Lucke D 

PROVIDER: S-EPMC10695670 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature

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Access to Naphthoic Acid Derivatives through an Oxabenzonorbornadiene Rearrangement.

Lücke Daniel D   Campbell Alexander S AS   Petzold Martin M   Sarpong Richmond R  

Organic letters 20231005 40

Herein, the synthesis of 1-hydroxy-2-naphthoic acid esters through an unexpected Lewis-acid-mediated 1,2-acyl shift of oxabenzonorbornadienes is reported. Using this methodology, novel substitution patterns for 1-hydroxy-2-naphtoic acid esters can be obtained. A mechanistic proposal and rationale for this transformation, the products of which had been previously incorrectly characterized, is given. ...[more]

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