An Acid-Catalyzed Epoxide Ring-Opening/Transesterification Cascade Cyclization to Diastereoselective Syntheses of (±)-β-Noscapine and (±)-β-Hydrastine

An acid-catalyzed stereoselective epoxide ring-opening/intramolecular transesterification cascade cyclization reaction and N-Boc deprotection was found to be a successful strategy to construct the phthalide tetrahydroisoquinoline skeleton in one pot. Based on this strategy, the unified and highly di...

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Veröffentlicht in:Organic letters 2019-09, Vol.21 (17), p.7149-7153
Hauptverfasser: Li, Jihui, Liu, Yongxiang, Song, Xinjing, Wu, Tianxiao, Meng, Jiaxin, Zheng, Yang, Qin, Qiaohua, Zhao, Dongmei, Cheng, Maosheng
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Sprache:eng
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Zusammenfassung:An acid-catalyzed stereoselective epoxide ring-opening/intramolecular transesterification cascade cyclization reaction and N-Boc deprotection was found to be a successful strategy to construct the phthalide tetrahydroisoquinoline skeleton in one pot. Based on this strategy, the unified and highly diastereoselective routes for the total syntheses of (±)-β-Noscapine and (±)-β-Hydrastine were exploited.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02715