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

ABSTRACT: 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 aldo...

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Autores principales: Xu, Wen-Dan, Li, Liang-Qun, Li, Ming-Ming, Geng, Hui-Chun, Qin, Hong-Bo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Berlin Heidelberg 2016
Materias:
Short Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5385656/
https://www.ncbi.nlm.nih.gov/pubmed/27095015
http://dx.doi.org/10.1007/s13659-016-0100-z
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author Xu, Wen-Dan
Li, Liang-Qun
Li, Ming-Ming
Geng, Hui-Chun
Qin, Hong-Bo
author_facet Xu, Wen-Dan
Li, Liang-Qun
Li, Ming-Ming
Geng, Hui-Chun
Qin, Hong-Bo
author_sort Xu, Wen-Dan
collection PubMed
description ABSTRACT: 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: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s13659-016-0100-z) contains supplementary material, which is available to authorized users.
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spelling pubmed-53856562017-04-24 Catalytic Asymmetric Formal Total Synthesis of (−)-Triptophenolide and (+)-Triptolide Xu, Wen-Dan Li, Liang-Qun Li, Ming-Ming Geng, Hui-Chun Qin, Hong-Bo Nat Prod Bioprospect Short Communication ABSTRACT: 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: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s13659-016-0100-z) contains supplementary material, which is available to authorized users. Springer Berlin Heidelberg 2016-04-20 /pmc/articles/PMC5385656/ /pubmed/27095015 http://dx.doi.org/10.1007/s13659-016-0100-z Text en © The Author(s) 2016 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
spellingShingle Short Communication
Xu, Wen-Dan
Li, Liang-Qun
Li, Ming-Ming
Geng, Hui-Chun
Qin, Hong-Bo
Catalytic Asymmetric Formal Total Synthesis of (−)-Triptophenolide and (+)-Triptolide
title Catalytic Asymmetric Formal Total Synthesis of (−)-Triptophenolide and (+)-Triptolide
title_full Catalytic Asymmetric Formal Total Synthesis of (−)-Triptophenolide and (+)-Triptolide
title_fullStr Catalytic Asymmetric Formal Total Synthesis of (−)-Triptophenolide and (+)-Triptolide
title_full_unstemmed Catalytic Asymmetric Formal Total Synthesis of (−)-Triptophenolide and (+)-Triptolide
title_short Catalytic Asymmetric Formal Total Synthesis of (−)-Triptophenolide and (+)-Triptolide
title_sort catalytic asymmetric formal total synthesis of (−)-triptophenolide and (+)-triptolide
topic Short Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5385656/
https://www.ncbi.nlm.nih.gov/pubmed/27095015
http://dx.doi.org/10.1007/s13659-016-0100-z
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