Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 675-678 |
| Seitenumfang | 4 |
| Fachzeitschrift | Organic letters |
| Jahrgang | 22 |
| Ausgabenummer | 2 |
| Frühes Online-Datum | 7 Jan. 2020 |
| Publikationsstatus | Veröffentlicht - 17 Jan. 2020 |
| Extern publiziert | Ja |
Abstract
A concise synthesis of yaequinolones J1 and J2 is reported. The route is based on the aryne insertion into the σ-C-N bond of an unsymmetric imide followed by a diastereoselective aldol cyclization of the resulting N-acylated aminobenzophenone. The chromene motif is generated in the first step by an organocatalytic tandem Knoevenagel electrocyclization of citral and 2-bromoresorcinol. The approach adheres to the ideality principle, using almost exclusively strategic bond-forming reactions.
ASJC Scopus Sachgebiete
- Biochemie, Genetik und Molekularbiologie (insg.)
- Biochemie
- Chemie (insg.)
- Physikalische und Theoretische Chemie
- Chemie (insg.)
- Organische Chemie
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in: Organic letters, Jahrgang 22, Nr. 2, 17.01.2020, S. 675-678.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Five-Step Synthesis of Yaequinolones J1 and J2
AU - Schwan, Johannes
AU - Kleoff, Merlin
AU - Heretsch, Philipp
AU - Christmann, Mathias
N1 - Funding Information: We thank Christiane Groneberg (FU Berlin) for chiral HPLC separation of (+)- and (−)-benzophenone 8 . We acknowledge the assistance of the Core Facility BioSupraMol supported by the DFG.
PY - 2020/1/17
Y1 - 2020/1/17
N2 - A concise synthesis of yaequinolones J1 and J2 is reported. The route is based on the aryne insertion into the σ-C-N bond of an unsymmetric imide followed by a diastereoselective aldol cyclization of the resulting N-acylated aminobenzophenone. The chromene motif is generated in the first step by an organocatalytic tandem Knoevenagel electrocyclization of citral and 2-bromoresorcinol. The approach adheres to the ideality principle, using almost exclusively strategic bond-forming reactions.
AB - A concise synthesis of yaequinolones J1 and J2 is reported. The route is based on the aryne insertion into the σ-C-N bond of an unsymmetric imide followed by a diastereoselective aldol cyclization of the resulting N-acylated aminobenzophenone. The chromene motif is generated in the first step by an organocatalytic tandem Knoevenagel electrocyclization of citral and 2-bromoresorcinol. The approach adheres to the ideality principle, using almost exclusively strategic bond-forming reactions.
UR - http://www.scopus.com/inward/record.url?scp=85078355156&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.9b04455
DO - 10.1021/acs.orglett.9b04455
M3 - Article
VL - 22
SP - 675
EP - 678
JO - Organic letters
JF - Organic letters
SN - 1523-7060
IS - 2
ER -