Abstract
A series of 4-substituted 5,6,7,9-tetrahydropyrrolo[2,3-f]indolizin-9-ones, representing the tricyclic core skeleton of ugibohlin, isophakellin, and styloguanidine, were synthesized via an intramolecular Vilsmeier-Haack reaction. This reaction allows the chemoselective C-C bond formation between the pyrrole C3 and proline C5 of N-[(pyrrol-2-yl)carbonyl]prolinamides to construct the B-ring without the protection of the pyrrole nitrogen. Unexpected oxidizative property of the tricyclic core skeleton was observed, which could illuminate understanding of the biological formation of these marine secondary metabolites.
| Original language | English |
|---|---|
| Pages (from-to) | 10459-10468 |
| Number of pages | 10 |
| Journal | Journal of Organic Chemistry |
| Volume | 78 |
| Issue number | 20 |
| DOIs | |
| Publication status | Published - 2013 Oct 18 |
Fingerprint
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Synthesis and unexpected oxidization of the tricyclic core of ugibohlin, isophakellin, and styloguanidine. / Chang, Chia Wei; Wu, Chi Cheng; Chang, Yung Yu; Lin, Chia Chi; Chien, Tun-Cheng.
In: Journal of Organic Chemistry, Vol. 78, No. 20, 18.10.2013, p. 10459-10468.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis and unexpected oxidization of the tricyclic core of ugibohlin, isophakellin, and styloguanidine
AU - Chang, Chia Wei
AU - Wu, Chi Cheng
AU - Chang, Yung Yu
AU - Lin, Chia Chi
AU - Chien, Tun-Cheng
PY - 2013/10/18
Y1 - 2013/10/18
N2 - A series of 4-substituted 5,6,7,9-tetrahydropyrrolo[2,3-f]indolizin-9-ones, representing the tricyclic core skeleton of ugibohlin, isophakellin, and styloguanidine, were synthesized via an intramolecular Vilsmeier-Haack reaction. This reaction allows the chemoselective C-C bond formation between the pyrrole C3 and proline C5 of N-[(pyrrol-2-yl)carbonyl]prolinamides to construct the B-ring without the protection of the pyrrole nitrogen. Unexpected oxidizative property of the tricyclic core skeleton was observed, which could illuminate understanding of the biological formation of these marine secondary metabolites.
AB - A series of 4-substituted 5,6,7,9-tetrahydropyrrolo[2,3-f]indolizin-9-ones, representing the tricyclic core skeleton of ugibohlin, isophakellin, and styloguanidine, were synthesized via an intramolecular Vilsmeier-Haack reaction. This reaction allows the chemoselective C-C bond formation between the pyrrole C3 and proline C5 of N-[(pyrrol-2-yl)carbonyl]prolinamides to construct the B-ring without the protection of the pyrrole nitrogen. Unexpected oxidizative property of the tricyclic core skeleton was observed, which could illuminate understanding of the biological formation of these marine secondary metabolites.
UR - http://www.scopus.com/inward/record.url?scp=84886376530&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84886376530&partnerID=8YFLogxK
U2 - 10.1021/jo401911a
DO - 10.1021/jo401911a
M3 - Article
C2 - 24050807
AN - SCOPUS:84886376530
VL - 78
SP - 10459
EP - 10468
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 20
ER -