Total Synthesis of Cyclotripeptidic Natural Products Anacine, Aurantiomide C, Polonimides A and C, and Verrucine F
The total synthesis of cyclotripeptidic natural products possessing a central piperazino[2,1-b]quinazolin-3,6-dione core is described through an original strategy involving the pivotal cyclocondensation of an electrophilic homoserine lactone intermediate. The alkylidene group was spontaneously installed by autoxidation during the cyclocondensation process, while the propionamide side chain was introduced through the nickel-catalyzed aminocarbonylation of a bromoethyl intermediate. This last reaction is unprecedented on such highly functionalized intermediates. Finally, we explored structural modifications and interconversions of the natural products. Overall, this work led to anacine, aurantiomide C, polonimides A and C, and verrucine F.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2024 |
|---|---|
| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:26 |
|---|---|
| Enthalten in: |
Organic letters - 26(2024), 13 vom: 05. Apr., Seite 2629-2634 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Han, Guanghui [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
|---|
| Anmerkungen: |
Date Revised 05.04.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
|---|
| doi: |
10.1021/acs.orglett.4c00658 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM370195000 |
|---|
| LEADER | 01000caa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM370195000 | ||
| 003 | DE-627 | ||
| 005 | 20240405233954.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 240327s2024 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1021/acs.orglett.4c00658 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1366.xml |
| 035 | |a (DE-627)NLM370195000 | ||
| 035 | |a (NLM)38529937 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Han, Guanghui |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Total Synthesis of Cyclotripeptidic Natural Products Anacine, Aurantiomide C, Polonimides A and C, and Verrucine F |
| 264 | 1 | |c 2024 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Revised 05.04.2024 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a The total synthesis of cyclotripeptidic natural products possessing a central piperazino[2,1-b]quinazolin-3,6-dione core is described through an original strategy involving the pivotal cyclocondensation of an electrophilic homoserine lactone intermediate. The alkylidene group was spontaneously installed by autoxidation during the cyclocondensation process, while the propionamide side chain was introduced through the nickel-catalyzed aminocarbonylation of a bromoethyl intermediate. This last reaction is unprecedented on such highly functionalized intermediates. Finally, we explored structural modifications and interconversions of the natural products. Overall, this work led to anacine, aurantiomide C, polonimides A and C, and verrucine F | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Zhang, Wei |e verfasserin |4 aut | |
| 700 | 1 | |a Acs, Emmanuelle |e verfasserin |4 aut | |
| 700 | 1 | |a Paquin, Alexis |e verfasserin |4 aut | |
| 700 | 1 | |a Ronzon, Quentin |e verfasserin |4 aut | |
| 700 | 1 | |a Casaretto, Nicolas |e verfasserin |4 aut | |
| 700 | 1 | |a Nay, Bastien |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Organic letters |d 1999 |g 26(2024), 13 vom: 05. Apr., Seite 2629-2634 |w (DE-627)NLM106817639 |x 1523-7052 |7 nnns |
| 773 | 1 | 8 | |g volume:26 |g year:2024 |g number:13 |g day:05 |g month:04 |g pages:2629-2634 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1021/acs.orglett.4c00658 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 26 |j 2024 |e 13 |b 05 |c 04 |h 2629-2634 | ||