Issue 44, 2024

Concise syntheses of (–)-quinocarcinol methyl ester and (–)-oxa-quinocarcinol methyl ester

Abstract

A concise synthesis of (–)-quinocarcinol methyl ester was accomplished with an overall yield of 39% through a 9-step longest linear sequence (LLS). Our synthesis features a two-step ester reduction/reductive amination sequence, a stereoselective [3 + 2] intramolecular cross-cycloaddition for the construction of bicyclo[3.2.1]octane skeletons, four simultaneous hydrogenolysis reactions in a one-pot process, and a stereoselective Krapcho decarboxylation. By following this protocol, (–)-oxa-quinocarcinol methyl ester was also achieved.

Graphical abstract: Concise syntheses of (–)-quinocarcinol methyl ester and (–)-oxa-quinocarcinol methyl ester

Supplementary files

Article information

Article type
Communication
Submitted
18 Aug 2024
Accepted
01 Oct 2024
First published
02 Oct 2024

Org. Biomol. Chem., 2024,22, 8724-8729

Concise syntheses of (–)-quinocarcinol methyl ester and (–)-oxa-quinocarcinol methyl ester

T. Song, Y. Wu, J. Ren and Z. Wang, Org. Biomol. Chem., 2024, 22, 8724 DOI: 10.1039/D4OB01363H

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