A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky
2011 ◽
Vol 7
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pp. 1342-1346
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Keyword(s):
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.