Biomimetic Phosphate-Catalyzed Pictet–Spengler Reaction for the Synthesis of 1,1′-Disubstituted and Spiro-Tetrahydroisoquinoline Alkaloids

[Image: see text] Tetrahydroisoquinoline (THIQ) alkaloids are an important group of compounds that exhibit a range of bioactivities. Here, a phosphate buffer-catalyzed Pictet–Spengler reaction (PSR) using unreactive ketone substrates is described. A variety of 1,1′-disubstituted and spiro-tetrahydro...

Descripción completa

Detalles Bibliográficos
Autores principales: Zhao, Jianxiong, Méndez-Sánchez, Daniel, Ward, John M., Hailes, Helen C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7007230/
https://www.ncbi.nlm.nih.gov/pubmed/31095375
http://dx.doi.org/10.1021/acs.joc.9b00527
_version_ 1783495286827515904
author Zhao, Jianxiong
Méndez-Sánchez, Daniel
Ward, John M.
Hailes, Helen C.
author_facet Zhao, Jianxiong
Méndez-Sánchez, Daniel
Ward, John M.
Hailes, Helen C.
author_sort Zhao, Jianxiong
collection PubMed
description [Image: see text] Tetrahydroisoquinoline (THIQ) alkaloids are an important group of compounds that exhibit a range of bioactivities. Here, a phosphate buffer-catalyzed Pictet–Spengler reaction (PSR) using unreactive ketone substrates is described. A variety of 1,1′-disubstituted and spiro-tetrahydroisoquinoline alkaloids were readily prepared in one-step and high yields, highlighting the general applicability of this approach. This study features the role of phosphate in the aqueous-based PSR and provides an atom-efficient, sustainable route to new THIQs.
format Online
Article
Text
id pubmed-7007230
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-70072302020-02-10 Biomimetic Phosphate-Catalyzed Pictet–Spengler Reaction for the Synthesis of 1,1′-Disubstituted and Spiro-Tetrahydroisoquinoline Alkaloids Zhao, Jianxiong Méndez-Sánchez, Daniel Ward, John M. Hailes, Helen C. J Org Chem [Image: see text] Tetrahydroisoquinoline (THIQ) alkaloids are an important group of compounds that exhibit a range of bioactivities. Here, a phosphate buffer-catalyzed Pictet–Spengler reaction (PSR) using unreactive ketone substrates is described. A variety of 1,1′-disubstituted and spiro-tetrahydroisoquinoline alkaloids were readily prepared in one-step and high yields, highlighting the general applicability of this approach. This study features the role of phosphate in the aqueous-based PSR and provides an atom-efficient, sustainable route to new THIQs. American Chemical Society 2019-05-16 2019-06-21 /pmc/articles/PMC7007230/ /pubmed/31095375 http://dx.doi.org/10.1021/acs.joc.9b00527 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Zhao, Jianxiong
Méndez-Sánchez, Daniel
Ward, John M.
Hailes, Helen C.
Biomimetic Phosphate-Catalyzed Pictet–Spengler Reaction for the Synthesis of 1,1′-Disubstituted and Spiro-Tetrahydroisoquinoline Alkaloids
title Biomimetic Phosphate-Catalyzed Pictet–Spengler Reaction for the Synthesis of 1,1′-Disubstituted and Spiro-Tetrahydroisoquinoline Alkaloids
title_full Biomimetic Phosphate-Catalyzed Pictet–Spengler Reaction for the Synthesis of 1,1′-Disubstituted and Spiro-Tetrahydroisoquinoline Alkaloids
title_fullStr Biomimetic Phosphate-Catalyzed Pictet–Spengler Reaction for the Synthesis of 1,1′-Disubstituted and Spiro-Tetrahydroisoquinoline Alkaloids
title_full_unstemmed Biomimetic Phosphate-Catalyzed Pictet–Spengler Reaction for the Synthesis of 1,1′-Disubstituted and Spiro-Tetrahydroisoquinoline Alkaloids
title_short Biomimetic Phosphate-Catalyzed Pictet–Spengler Reaction for the Synthesis of 1,1′-Disubstituted and Spiro-Tetrahydroisoquinoline Alkaloids
title_sort biomimetic phosphate-catalyzed pictet–spengler reaction for the synthesis of 1,1′-disubstituted and spiro-tetrahydroisoquinoline alkaloids
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7007230/
https://www.ncbi.nlm.nih.gov/pubmed/31095375
http://dx.doi.org/10.1021/acs.joc.9b00527
work_keys_str_mv AT zhaojianxiong biomimeticphosphatecatalyzedpictetspenglerreactionforthesynthesisof11disubstitutedandspirotetrahydroisoquinolinealkaloids
AT mendezsanchezdaniel biomimeticphosphatecatalyzedpictetspenglerreactionforthesynthesisof11disubstitutedandspirotetrahydroisoquinolinealkaloids
AT wardjohnm biomimeticphosphatecatalyzedpictetspenglerreactionforthesynthesisof11disubstitutedandspirotetrahydroisoquinolinealkaloids
AT haileshelenc biomimeticphosphatecatalyzedpictetspenglerreactionforthesynthesisof11disubstitutedandspirotetrahydroisoquinolinealkaloids

Ejemplares similares