Total Synthesis of Pactalactam, an Imidazolidinone-Type Pactamycin Analogue

Taejung Kim, Shohei Matsushita, So Matsudaira, Tsuyoshi Doi, Shinji Hirota, Young Tae Park, Masayuki Igarashi, Masaki Hatano, Noriko Ikeda, Jungyeob Ham, Masaya Nakata, Yoko Saikawa

研究成果: Article査読

6 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)3554-3557
ページ数4
ジャーナルOrganic Letters
21
10
DOI
出版ステータスPublished - 2019 5 17

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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