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Total Synthesis of Pactalactam, an Imidazolidinone-Type Pactamycin Analogue
Kim, Taejung,Matsushita, Shohei,Matsudaira, So,Doi, Tsuyoshi,Hirota, Shinji,Park, Young-Tae,Igarashi, Masayuki,Hatano, Masaki,Ikeda, Noriko,Ham, Jungyeob,Nakata, Masaya,Saikawa, Yoko THE AMERICAN CHEMICAL SOCIETY 2019 ORGANIC LETTERS Vol.21 No.10
<P>The first total synthesis of pactalactam was accomplished using substrate-controlled stereoselective aziridination and regioselective aziridine ring-opening to construct three continuous amino groups on an octasubstituted cyclopentane core. The cyclopentane framework was obtained by ring-closing metathesis and aldol coupling using a <SMALL>L</SMALL>-threonine-derived oxazoline compound. Cyclic urea formation, <I>m</I>-acetylphenyl group introduction by Chan-Lam coupling, and primary alcohol-selective acylation yielded the reported pactalactam structure. The presence of pactalactam in the fermentation broth of pactamycin-producing bacteria was also confirmed.</P> [FIG OMISSION]</BR>