301346-38-3Relevant academic research and scientific papers
A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky
Zhao, Guolei,Yang, Chao,Li, Bing,Xia, Wujiong
, p. 1342 - 1346 (2011/11/14)
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.
First total synthesis of Aspinolide B, a new pentaketide produced by Aspergillus ochraceus
Pilli, Ronaldo A.,Victor, Mauricio M.,De Meijere, Armin
, p. 5910 - 5916 (2007/10/03)
The first asymmetric total synthesis of Aspinolide B (1), a new 10-membered lactone discovered by chemical screening methods in the cultures of Aspergillus ochraceus, has been accomplished. The key steps included a selective Felkin-type addition of TMS-acetylene to aldehyde 3a and a Nozaki-Hiyama-Kishi coupling reaction to build the required 10-membered ring. This synthesis confirmed the absolute stereochemistry of aspinolide B, established through Helmchen's method and corrected its previously reported specific optical rotation.
