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

Research output: Contribution to journalArticle

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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Pactamycin
Cyclopentanes
broths
analogs
acylation
Acylation
fermentation
metathesis
rings
Threonine
closing
synthesis
ureas
Fermentation
bacteria
Urea
Bacteria
alcohols
Alcohols
Substrates

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., ... 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

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.

In: Organic Letters, Vol. 21, No. 10, 17.05.2019, p. 3554-3557.

Research output: Contribution to journalArticle

Kim, T, Matsushita, S, Matsudaira, S, Doi, T, Hirota, S, Park, YT, Igarashi, M, Hatano, M, Ikeda, N, Ham, J, Nakata, M & Saikawa, Y 2019, 'Total Synthesis of Pactalactam, an Imidazolidinone-Type Pactamycin Analogue', Organic Letters, vol. 21, no. 10, pp. 3554-3557. https://doi.org/10.1021/acs.orglett.9b00905
Kim T, Matsushita S, Matsudaira S, Doi T, Hirota S, Park YT et al. Total Synthesis of Pactalactam, an Imidazolidinone-Type Pactamycin Analogue. Organic Letters. 2019 May 17;21(10):3554-3557. https://doi.org/10.1021/acs.orglett.9b00905
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. / Total Synthesis of Pactalactam, an Imidazolidinone-Type Pactamycin Analogue. In: Organic Letters. 2019 ; Vol. 21, No. 10. pp. 3554-3557.
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