Details
| Original language | English |
|---|---|
| Pages (from-to) | 7661-7664 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 20 |
| Issue number | 23 |
| Early online date | 27 Nov 2018 |
| Publication status | Published - 7 Dec 2018 |
| Externally published | Yes |
Abstract
A general strategy for the synthesis of 3,4-dioxygenated quinolin-2-one natural products is reported. The key step is a regioselective insertion of arynes into unsymmetric imides. When performed in continuous flow, the reaction proceeds within minutes, while lower yields and longer reaction times are observed in batch. The resulting N-acylated 2-aminobenzophenones were transformed to (±)-peniprequinolone, (±)-aflaquinolones E and F, (±)-6-deoxyaflaquinolone E, (±)-quinolinones A and B, and (±)-aniduquinolone C in 1-3 steps.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic Letters, Vol. 20, No. 23, 07.12.2018, p. 7661-7664.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis of Quinolinone Alkaloids via Aryne Insertions into Unsymmetric Imides in Flow
AU - Schwan, Johannes
AU - Kleoff, Merlin
AU - Hartmayer, Bence
AU - Heretsch, Philipp
AU - Christmann, Mathias
N1 - Publisher Copyright: © 2018 American Chemical Society.
PY - 2018/12/7
Y1 - 2018/12/7
N2 - A general strategy for the synthesis of 3,4-dioxygenated quinolin-2-one natural products is reported. The key step is a regioselective insertion of arynes into unsymmetric imides. When performed in continuous flow, the reaction proceeds within minutes, while lower yields and longer reaction times are observed in batch. The resulting N-acylated 2-aminobenzophenones were transformed to (±)-peniprequinolone, (±)-aflaquinolones E and F, (±)-6-deoxyaflaquinolone E, (±)-quinolinones A and B, and (±)-aniduquinolone C in 1-3 steps.
AB - A general strategy for the synthesis of 3,4-dioxygenated quinolin-2-one natural products is reported. The key step is a regioselective insertion of arynes into unsymmetric imides. When performed in continuous flow, the reaction proceeds within minutes, while lower yields and longer reaction times are observed in batch. The resulting N-acylated 2-aminobenzophenones were transformed to (±)-peniprequinolone, (±)-aflaquinolones E and F, (±)-6-deoxyaflaquinolone E, (±)-quinolinones A and B, and (±)-aniduquinolone C in 1-3 steps.
UR - http://www.scopus.com/inward/record.url?scp=85058288548&partnerID=8YFLogxK
U2 - 10.26434/chemrxiv.7241501.v1
DO - 10.26434/chemrxiv.7241501.v1
M3 - Article
VL - 20
SP - 7661
EP - 7664
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 23
ER -