Mild Approach to Nucleoside Analogues via Photoredox/Cu-Catalyzed Decarboxylative C-N Bond Formation. Total Synthesis of Oxetanocin A
The conventional N-glycosylation methods for nucleoside synthesis usually require strongly acidic or basic conditions. Here we report the decarboxylative C(sp3)-N coupling of glycosyl N-hydroxyphthalimide esters with nucleobases via dual photoredox/Cu catalysis, which offered a mild approach to nucleoside analogues. A total synthesis of oxetanocin A, an antiviral natural product containing an oxetanose moiety, has been achieved by using this method.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2024 |
|---|---|
| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:26 |
|---|---|
| Enthalten in: |
Organic letters - 26(2024), 14 vom: 12. Apr., Seite 2691-2696 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Wang, Ruonan [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
|---|
| Anmerkungen: |
Date Revised 12.04.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
|---|
| doi: |
10.1021/acs.orglett.3c00914 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM365024961 |
|---|
| LEADER | 01000caa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM365024961 | ||
| 003 | DE-627 | ||
| 005 | 20240412232609.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231226s2024 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1021/acs.orglett.3c00914 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1373.xml |
| 035 | |a (DE-627)NLM365024961 | ||
| 035 | |a (NLM)38011311 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Wang, Ruonan |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Mild Approach to Nucleoside Analogues via Photoredox/Cu-Catalyzed Decarboxylative C-N Bond Formation. Total Synthesis of Oxetanocin A |
| 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 12.04.2024 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a The conventional N-glycosylation methods for nucleoside synthesis usually require strongly acidic or basic conditions. Here we report the decarboxylative C(sp3)-N coupling of glycosyl N-hydroxyphthalimide esters with nucleobases via dual photoredox/Cu catalysis, which offered a mild approach to nucleoside analogues. A total synthesis of oxetanocin A, an antiviral natural product containing an oxetanose moiety, has been achieved by using this method | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Xu, Hao |e verfasserin |4 aut | |
| 700 | 1 | |a Banerjee, Arpan |e verfasserin |4 aut | |
| 700 | 1 | |a Cui, Zhongwen |e verfasserin |4 aut | |
| 700 | 1 | |a Ma, Yuyong |e verfasserin |4 aut | |
| 700 | 1 | |a Whittingham, William G |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Peng |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Ang |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Organic letters |d 1999 |g 26(2024), 14 vom: 12. Apr., Seite 2691-2696 |w (DE-627)NLM106817639 |x 1523-7052 |7 nnns |
| 773 | 1 | 8 | |g volume:26 |g year:2024 |g number:14 |g day:12 |g month:04 |g pages:2691-2696 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1021/acs.orglett.3c00914 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 26 |j 2024 |e 14 |b 12 |c 04 |h 2691-2696 | ||