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Updated: Oct 1, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Synthesis and Reactivity of 1-Hydroxyherquline A
Thomas T Kim1, Chungwoo Lee1, Dongwook Kim2
1Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Republic of Korea.
Abstract:
Herein, we present the synthesis of 1-hydroxyherquline A and describe its reactivity discovered during its attempted conversion to herquline A, a long-sought natural product target in the synthetic chemical community. The strategic installation of the C1 hydroxyl group enabled the key aza-Michael addition-mediated N10-C2 bond formation and eventually access to 1-hydroxyherquline A, the most advanced herquline A congener reported to date. Our attempted reductive transformation of 1-hydroxyherquline A to herquline A was challenged by the extremely strained bowl-shaped pentacyclic structures of key precursors that prevented either radical formation at C1 or protonation (or hydrogenation) from the desired face. These discoveries regarding the innate chemical reactivities of advanced intermediates toward herquline A may prove useful in efforts toward this formidable target.
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