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Application of the Asymmetric Pictet–Spengler Reaction in the Total Synthesis of Natural Products and Relevant Biologically Active Compounds

Tetrahydroisoquinolines are the framework of numerous natural products predominantly alkaloids, an important and one of the most wide spread families of naturally occurring compounds in the plant kingdom. Tetrahydroisoquinolines are commonly constructed through an old reaction, the so-called Pictet–...

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Autores principales: M. Heravi, Majid, Zadsirjan, Vahideh, Malmir, Masumeh
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017108/
https://www.ncbi.nlm.nih.gov/pubmed/29670061
http://dx.doi.org/10.3390/molecules23040943
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author M. Heravi, Majid
Zadsirjan, Vahideh
Malmir, Masumeh
author_facet M. Heravi, Majid
Zadsirjan, Vahideh
Malmir, Masumeh
author_sort M. Heravi, Majid
collection PubMed
description Tetrahydroisoquinolines are the framework of numerous natural products predominantly alkaloids, an important and one of the most wide spread families of naturally occurring compounds in the plant kingdom. Tetrahydroisoquinolines are commonly constructed through an old reaction, the so-called Pictet–Spengler Reaction (PSR). In this reaction, a β-aryl ethylamine undergoes an acid mediated condensation with a suitable aldehyde or ketone, followed by ring closure. In this review, we aim to highlight the applications of the asymmetric variant of this old name reaction in the total synthesis of natural products, chiefly, alkaloids, which exhibit significant biological properties.
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spelling pubmed-60171082018-11-13 Application of the Asymmetric Pictet–Spengler Reaction in the Total Synthesis of Natural Products and Relevant Biologically Active Compounds M. Heravi, Majid Zadsirjan, Vahideh Malmir, Masumeh Molecules Review Tetrahydroisoquinolines are the framework of numerous natural products predominantly alkaloids, an important and one of the most wide spread families of naturally occurring compounds in the plant kingdom. Tetrahydroisoquinolines are commonly constructed through an old reaction, the so-called Pictet–Spengler Reaction (PSR). In this reaction, a β-aryl ethylamine undergoes an acid mediated condensation with a suitable aldehyde or ketone, followed by ring closure. In this review, we aim to highlight the applications of the asymmetric variant of this old name reaction in the total synthesis of natural products, chiefly, alkaloids, which exhibit significant biological properties. MDPI 2018-04-18 /pmc/articles/PMC6017108/ /pubmed/29670061 http://dx.doi.org/10.3390/molecules23040943 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Review
M. Heravi, Majid
Zadsirjan, Vahideh
Malmir, Masumeh
Application of the Asymmetric Pictet–Spengler Reaction in the Total Synthesis of Natural Products and Relevant Biologically Active Compounds
title Application of the Asymmetric Pictet–Spengler Reaction in the Total Synthesis of Natural Products and Relevant Biologically Active Compounds
title_full Application of the Asymmetric Pictet–Spengler Reaction in the Total Synthesis of Natural Products and Relevant Biologically Active Compounds
title_fullStr Application of the Asymmetric Pictet–Spengler Reaction in the Total Synthesis of Natural Products and Relevant Biologically Active Compounds
title_full_unstemmed Application of the Asymmetric Pictet–Spengler Reaction in the Total Synthesis of Natural Products and Relevant Biologically Active Compounds
title_short Application of the Asymmetric Pictet–Spengler Reaction in the Total Synthesis of Natural Products and Relevant Biologically Active Compounds
title_sort application of the asymmetric pictet–spengler reaction in the total synthesis of natural products and relevant biologically active compounds
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017108/
https://www.ncbi.nlm.nih.gov/pubmed/29670061
http://dx.doi.org/10.3390/molecules23040943
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