@article{0109b844f79043f6983656fd6e940a21,
title = "Total Synthesis of Pactalactam, an Imidazolidinone-Type Pactamycin Analogue",
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.",
author = "Taejung Kim and Shohei Matsushita and So Matsudaira and Tsuyoshi Doi and Shinji Hirota and Park, {Young Tae} and Masayuki Igarashi and Masaki Hatano and Noriko Ikeda and Jungyeob Ham and Masaya Nakata and Yoko Saikawa",
note = "Funding Information: We thank Dr. Ryuuichi Sawa (Institute of Microbial Chemistry) for analyzing the culture medium extract by LC/ MS/MS, Dr. Jae Kyun Lee (Korea Institute of Science and Technology) for X-ray structure determination, and Mr. Daisuke Tanaka (Keio University) for early contributions to this work. This work was partially supported by the Korea Institute of Science and Technology (KIST) institutional program (Project No. 2Z05610) and by the Nano Convergence Industrial Strategic Technology Development Program (No. 20000105) funded by the Ministry of Trade, Industry & Energy (MOTIE, Korea).",
year = "2019",
month = may,
day = "17",
doi = "10.1021/acs.orglett.9b00905",
language = "English",
volume = "21",
pages = "3554--3557",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "10",
}