Total Synthesis of the Racemate of Laurolitsine
The total synthesis of laurolitsine was achieved for the first time. This reaction was accomplished in 14 steps with a 2.3% yield (this was calculated using 3-hydroxy-4-methoxybenzaldehyde as the starting material) starting from two simple materials, 3-hydroxy-4-methoxybenzaldehyde and 2-(3-hydroxy-4-methoxyphenyl)acetic acid, and the longest linear sequence consisted of 11 steps. The key steps included an electrophilic addition reaction in which a nitro group was reduced to an amino group using lithium tetrahydroaluminum and a Pd-catalyzed direct biaryl coupling reaction. In this paper, many of the experimental steps were optimized, and an innovative postprocessing method in which 2-(3-(benzyloxy)-4-methoxyphenyl)ethanamine is salted with oxalic acid was proposed.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2024 |
|---|---|
| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:29 |
|---|---|
| Enthalten in: |
Molecules (Basel, Switzerland) - 29(2024), 3 vom: 05. Feb. |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Cao, Mingyu [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
Aporphine alkaloid |
|---|
| Anmerkungen: |
Date Revised 12.02.2024 published: Electronic Citation Status PubMed-not-MEDLINE |
|---|
| doi: |
10.3390/molecules29030745 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM368279774 |
|---|
| LEADER | 01000caa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM368279774 | ||
| 003 | DE-627 | ||
| 005 | 20240212232153.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 240210s2024 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.3390/molecules29030745 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1289.xml |
| 035 | |a (DE-627)NLM368279774 | ||
| 035 | |a (NLM)38338488 | ||
| 035 | |a (PII)745 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Cao, Mingyu |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Total Synthesis of the Racemate of Laurolitsine |
| 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 12.02.2024 | ||
| 500 | |a published: Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a The total synthesis of laurolitsine was achieved for the first time. This reaction was accomplished in 14 steps with a 2.3% yield (this was calculated using 3-hydroxy-4-methoxybenzaldehyde as the starting material) starting from two simple materials, 3-hydroxy-4-methoxybenzaldehyde and 2-(3-hydroxy-4-methoxyphenyl)acetic acid, and the longest linear sequence consisted of 11 steps. The key steps included an electrophilic addition reaction in which a nitro group was reduced to an amino group using lithium tetrahydroaluminum and a Pd-catalyzed direct biaryl coupling reaction. In this paper, many of the experimental steps were optimized, and an innovative postprocessing method in which 2-(3-(benzyloxy)-4-methoxyphenyl)ethanamine is salted with oxalic acid was proposed | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a aporphine alkaloid | |
| 650 | 4 | |a laurolitsine | |
| 650 | 4 | |a synthetic route | |
| 650 | 4 | |a total synthesis | |
| 700 | 1 | |a Wang, Yiming |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Yong |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Caiyun |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Niangen |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Xiaopo |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Molecules (Basel, Switzerland) |d 2004 |g 29(2024), 3 vom: 05. Feb. |w (DE-627)NLM172073448 |x 1420-3049 |7 nnns |
| 773 | 1 | 8 | |g volume:29 |g year:2024 |g number:3 |g day:05 |g month:02 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.3390/molecules29030745 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 29 |j 2024 |e 3 |b 05 |c 02 | ||