Journal
ORGANIC LETTERS
Volume 24, Issue 10, Pages 1964-1968Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00379
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Funding
- National Research Foundation of Korea (NRF) - Korea government (MSIT) [2021R1A2C2011203, 2018R1A5A1025208]
- POSCO Science Fellowship of POSCO TJ Park Foundation
- National Research Foundation of Korea [2021R1A2C2011203] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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In this paper, we present the synthesis and reactivity of 1-hydroxyherquline A, and discuss the challenges encountered during its conversion to herquline A. These findings provide valuable insights for future research and synthesis of herquline A.
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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