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Updated: Jun 11, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Concise syntheses of (-)-quinocarcinol methyl ester and (-)-oxa-quinocarcinol methyl ester
Tianhang Song1, Yifan Wu1, Jun Ren1
1State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, PR China. wzwrj@nankai.edu.cn.
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.
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