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 | |
| Publication status | Published - 2019 May 17 |
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ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
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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TY - JOUR
T1 - Total Synthesis of Pactalactam, an Imidazolidinone-Type Pactamycin Analogue
AU - Kim, Taejung
AU - Matsushita, Shohei
AU - Matsudaira, So
AU - Doi, Tsuyoshi
AU - Hirota, Shinji
AU - Park, Young Tae
AU - Igarashi, Masayuki
AU - Hatano, Masaki
AU - Ikeda, Noriko
AU - Ham, Jungyeob
AU - Nakata, Masaya
AU - Saikawa, Yoko
PY - 2019/5/17
Y1 - 2019/5/17
N2 - 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.
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.
UR - http://www.scopus.com/inward/record.url?scp=85065837756&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85065837756&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.9b00905
DO - 10.1021/acs.orglett.9b00905
M3 - Article
C2 - 31058517
AN - SCOPUS:85065837756
VL - 21
SP - 3554
EP - 3557
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 10
ER -