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

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2 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3554-3557
Number of pages4
JournalOrganic Letters
Volume21
Issue number10
DOIs
Publication statusPublished - 2019 May 17

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Kim, T., Matsushita, S., Matsudaira, S., Doi, T., Hirota, S., Park, Y. T., Igarashi, M., Hatano, M., Ikeda, N., Ham, J., Nakata, M., & Saikawa, Y. (2019). Total Synthesis of Pactalactam, an Imidazolidinone-Type Pactamycin Analogue. Organic Letters, 21(10), 3554-3557. https://doi.org/10.1021/acs.orglett.9b00905