Total Synthesis of Pactalactam, an Imidazolidinone-Type Pactamycin Analogue.

Autor:	Kim T; Department of Applied Chemistry, Faculty of Science and Technology , Keio University , 3-14-1 Hiyoshi , Kohoku-ku, Yokohama 223-8522 , Japan.; Natural Products Research Institute , Korea Institute of Science and Technology (KIST) , 679 Saimdang-ro , Gangneung 25451 , Republic of Korea., Matsushita S; Department of Applied Chemistry, Faculty of Science and Technology , Keio University , 3-14-1 Hiyoshi , Kohoku-ku, Yokohama 223-8522 , Japan., Matsudaira S; Department of Applied Chemistry, Faculty of Science and Technology , Keio University , 3-14-1 Hiyoshi , Kohoku-ku, Yokohama 223-8522 , Japan., Doi T; Department of Applied Chemistry, Faculty of Science and Technology , Keio University , 3-14-1 Hiyoshi , Kohoku-ku, Yokohama 223-8522 , Japan., Hirota S; Department of Applied Chemistry, Faculty of Science and Technology , Keio University , 3-14-1 Hiyoshi , Kohoku-ku, Yokohama 223-8522 , Japan., Park YT; Natural Products Research Institute , Korea Institute of Science and Technology (KIST) , 679 Saimdang-ro , Gangneung 25451 , Republic of Korea., Igarashi M; Institute of Microbial Chemistry (BIKAKEN) , 3-14-23 Kamiosaki , Shinagawa-ku, Tokyo 141-0021 , Japan., Hatano M; Institute of Microbial Chemistry (BIKAKEN) , 3-14-23 Kamiosaki , Shinagawa-ku, Tokyo 141-0021 , Japan., Ikeda N; Institute of Microbial Chemistry (BIKAKEN) , 3-14-23 Kamiosaki , Shinagawa-ku, Tokyo 141-0021 , Japan., Ham J; Natural Products Research Institute , Korea Institute of Science and Technology (KIST) , 679 Saimdang-ro , Gangneung 25451 , Republic of Korea., Nakata M; Department of Applied Chemistry, Faculty of Science and Technology , Keio University , 3-14-1 Hiyoshi , Kohoku-ku, Yokohama 223-8522 , Japan., Saikawa Y; Department of Applied Chemistry, Faculty of Science and Technology , Keio University , 3-14-1 Hiyoshi , Kohoku-ku, Yokohama 223-8522 , Japan.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2019 May 17; Vol. 21 (10), pp. 3554-3557. Date of Electronic Publication: 2019 May 06.
DOI:	10.1021/acs.orglett.9b00905
Abstrakt:	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.
Databáze:	MEDLINE
Externí odkaz:	Zobrazit plný text záznamu