Catalytic Asymmetric Formal Total Synthesis of (−)-Triptophenolide and (+)-Triptolide

Catalytic asymmetric formal synthesis of (−)-Triptophenolide and (+)-Triptolide have been achieved. Key reaction involves Palladium catalyzed asymmetric conjugate addition of aryl boronic acid to 3-methyl cyclohexe-1-none to form quaternary carbon. Claisen rearrangement and subsequent aldol reaction...

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Veröffentlicht in:	Natural products and bioprospecting 2016-06, Vol.6 (3), p.183-186
Hauptverfasser:	Xu, Wen-Dan, Li, Liang-Qun, Li, Ming-Ming, Geng, Hui-Chun, Qin, Hong-Bo
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Sprache:	eng
Schlagworte:	Biomedical and Life Sciences Bioorganic Chemistry carbon catalytic activity chemical reactions Food Science Life Sciences Medicinal Chemistry palladium Pharmacology/Toxicology Plant Biochemistry Plant Sciences Short Communication
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creator	Xu, Wen-Dan Li, Liang-Qun Li, Ming-Ming Geng, Hui-Chun Qin, Hong-Bo
description	Catalytic asymmetric formal synthesis of (−)-Triptophenolide and (+)-Triptolide have been achieved. Key reaction involves Palladium catalyzed asymmetric conjugate addition of aryl boronic acid to 3-methyl cyclohexe-1-none to form quaternary carbon. Claisen rearrangement and subsequent aldol reaction furnished trans -decaline key intermediate, which assured a formal total synthesis of (−)-Triptophenolide and (+)-Triptolide. Graphical Abstract
doi_str_mv	10.1007/s13659-016-0100-z
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subjects	Biomedical and Life Sciences Bioorganic Chemistry carbon catalytic activity chemical reactions Food Science Life Sciences Medicinal Chemistry palladium Pharmacology/Toxicology Plant Biochemistry Plant Sciences Short Communication
title	Catalytic Asymmetric Formal Total Synthesis of (−)-Triptophenolide and (+)-Triptolide
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