A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky

A new phenylethyl alkyl amide, (10R)-10-hydroxy-N-phenethyloctadecanamide (1), was isolated from the beetle Ambrostoma quadriimpressum Motschulsky. The structure of the amide was determined by NMR and MS. The absolute configuration of compound 1 was confirmed by an asymmetric total synthesis, which...

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Detalles Bibliográficos
Autores principales: Zhao, Guolei, Yang, Chao, Li, Bing, Xia, Wujiong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201048/
https://www.ncbi.nlm.nih.gov/pubmed/22043245
http://dx.doi.org/10.3762/bjoc.7.158
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author Zhao, Guolei
Yang, Chao
Li, Bing
Xia, Wujiong
author_facet Zhao, Guolei
Yang, Chao
Li, Bing
Xia, Wujiong
author_sort Zhao, Guolei
collection PubMed
description A new phenylethyl alkyl amide, (10R)-10-hydroxy-N-phenethyloctadecanamide (1), was isolated from the beetle Ambrostoma quadriimpressum Motschulsky. The structure of the amide was determined by NMR and MS. The absolute configuration of compound 1 was confirmed by an asymmetric total synthesis, which was started from L-glutamic acid. The construction of the aliphatic chain was accomplished by the selective protection of the hydroxy groups and two-time implementation of the Wittig olefination reaction.
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spelling pubmed-32010482011-10-31 A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky Zhao, Guolei Yang, Chao Li, Bing Xia, Wujiong Beilstein J Org Chem Full Research Paper A new phenylethyl alkyl amide, (10R)-10-hydroxy-N-phenethyloctadecanamide (1), was isolated from the beetle Ambrostoma quadriimpressum Motschulsky. The structure of the amide was determined by NMR and MS. The absolute configuration of compound 1 was confirmed by an asymmetric total synthesis, which was started from L-glutamic acid. The construction of the aliphatic chain was accomplished by the selective protection of the hydroxy groups and two-time implementation of the Wittig olefination reaction. Beilstein-Institut 2011-09-29 /pmc/articles/PMC3201048/ /pubmed/22043245 http://dx.doi.org/10.3762/bjoc.7.158 Text en Copyright © 2011, Zhao 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
Zhao, Guolei
Yang, Chao
Li, Bing
Xia, Wujiong
A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky
title A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky
title_full A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky
title_fullStr A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky
title_full_unstemmed A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky
title_short A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky
title_sort new phenylethyl alkyl amide from the ambrostoma quadriimpressum motschulsky
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201048/
https://www.ncbi.nlm.nih.gov/pubmed/22043245
http://dx.doi.org/10.3762/bjoc.7.158
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