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

doi:10.1021/acs.orglett.9b00905

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

Department of Applied Chemistry

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	3554-3557
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.9b00905
Publication status	Published - 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

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 journal › Article

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AU - Igarashi, Masayuki

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AB - 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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10.1021/acs.orglett.9b00905