Total Synthesis of Pactalactam, an Imidazolidinone-Type Pactamycin Analogue

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 met...

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Published inOrganic letters Vol. 21; no. 10; pp. 3554 - 3557
Main Authors 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
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.05.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CORE
AZIRIDINES
INITIATION
ACIDS
CYCLOPENTANE
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Summary: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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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00905