Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step

The first organocatalytic asymmetric synthesis of smyrindiol, by using an (S)-proline catalyzed enantioselective intramolecular aldol reaction as the key step, is described. Smyrindiol was synthesized from commercially available 2,4-dihydroxybenzaldehyde in 15 steps, with excellent stereoselectivity...

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Autores principales: Enders, Dieter, Fronert, Jeanne, Bisschops, Tom, Boeck, Florian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458728/
https://www.ncbi.nlm.nih.gov/pubmed/23019438
http://dx.doi.org/10.3762/bjoc.8.123
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author Enders, Dieter
Fronert, Jeanne
Bisschops, Tom
Boeck, Florian
author_facet Enders, Dieter
Fronert, Jeanne
Bisschops, Tom
Boeck, Florian
author_sort Enders, Dieter
collection PubMed
description The first organocatalytic asymmetric synthesis of smyrindiol, by using an (S)-proline catalyzed enantioselective intramolecular aldol reaction as the key step, is described. Smyrindiol was synthesized from commercially available 2,4-dihydroxybenzaldehyde in 15 steps, with excellent stereoselectivity (de = 99%, ee = 99%). In the course of this total synthesis a new and mild coumarin assembly was developed.
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spelling pubmed-34587282012-09-27 Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step Enders, Dieter Fronert, Jeanne Bisschops, Tom Boeck, Florian Beilstein J Org Chem Full Research Paper The first organocatalytic asymmetric synthesis of smyrindiol, by using an (S)-proline catalyzed enantioselective intramolecular aldol reaction as the key step, is described. Smyrindiol was synthesized from commercially available 2,4-dihydroxybenzaldehyde in 15 steps, with excellent stereoselectivity (de = 99%, ee = 99%). In the course of this total synthesis a new and mild coumarin assembly was developed. Beilstein-Institut 2012-07-18 /pmc/articles/PMC3458728/ /pubmed/23019438 http://dx.doi.org/10.3762/bjoc.8.123 Text en Copyright © 2012, Enders et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Enders, Dieter
Fronert, Jeanne
Bisschops, Tom
Boeck, Florian
Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step
title Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step
title_full Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step
title_fullStr Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step
title_full_unstemmed Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step
title_short Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step
title_sort asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3458728/
https://www.ncbi.nlm.nih.gov/pubmed/23019438
http://dx.doi.org/10.3762/bjoc.8.123
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AT bisschopstom asymmetrictotalsynthesisofsmyrindiolemployinganorganocatalyticaldolkeystep
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