Total Synthesis of Pactalactam, an Imidazolidinone-Type Pactamycin Analogue
- Total Synthesis of Pactalactam, an Imidazolidinone-Type Pactamycin Analogue
- 함정엽; 박영태; 김태정; Shohei Matsushita; So Matsudaira; Tsuyoshi Doi; Shinji Hirota; Masayuki Igarashi; Masaki Hatano; Noriko Ikeda; Masaya Nakata; Yoko Saikawa
- total synthesis; pactamycin; pactalactam; derivative; Chan-Lam coupling
- Issue Date
- Organic letters
- VOL 21, NO 10-3557
- 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 l-threonine-derived oxazoline compound. Cyclic urea formation, m-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.
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