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Zhao G, Yang C, Li B, et al. A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky. Beilstein J Org Chem. 2011;7:1342-6doi: 10.3762/bjoc.7.158.
Zhao, G., Yang, C., Li, B., & Xia, W. (2011). A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky. Beilstein journal of organic chemistry, 71342-6. https://doi.org/10.3762/bjoc.7.158
Zhao, Guolei, et al. "A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky." Beilstein journal of organic chemistry vol. 7 (2011): 1342-6. doi: https://doi.org/10.3762/bjoc.7.158
Zhao G, Yang C, Li B, Xia W. A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky. Beilstein J Org Chem. 2011;7:1342-6. doi: 10.3762/bjoc.7.158. Epub 2011 Sep 29. PMID: 22043245; PMCID: PMC3201048.
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Beilstein J Org Chem. 2011;7:1342-6. doi: 10.3762/bjoc.7.158. Epub 2011 Sep 29.

A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky.

Beilstein journal of organic chemistry

Guolei Zhao, Chao Yang, Bing Li, Wujiong Xia

Affiliations

  1. State Key Lab of Urban Water Resource and Environment & the Academy of Fundamental and Interdisciplinary Sciences, Harbin Institute of Technology, Harbin 150080, China.

PMID: 22043245 PMCID: PMC3201048 DOI: 10.3762/bjoc.7.158

Abstract

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.

Keywords: asymmetric synthesis; beetle; fatty acid amide; isolation

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