Total Synthesis of Pactalactam, an Imidazolidinone-Type Pactamycin Analogue

Title
Total Synthesis of Pactalactam, an Imidazolidinone-Type Pactamycin Analogue
Authors
함정엽박영태김태정Shohei MatsushitaSo MatsudairaTsuyoshi DoiShinji HirotaMasayuki IgarashiMasaki HatanoNoriko IkedaMasaya NakataYoko Saikawa
Keywords
total synthesis; pactamycin; pactalactam; derivative; Chan-Lam coupling
Issue Date
2019-05
Publisher
Organic letters
Citation
VOL 21, NO 10-3557
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.
URI
http://pubs.kist.re.kr/handle/201004/69384
ISSN
1523-7060
Appears in Collections:
KIST Publication > Article
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