Details
Original language | English |
---|---|
Pages (from-to) | 675-678 |
Number of pages | 4 |
Journal | Organic letters |
Volume | 22 |
Issue number | 2 |
Early online date | 7 Jan 2020 |
Publication status | Published - 17 Jan 2020 |
Externally published | Yes |
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 subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
Cite this
- Standard
- Harvard
- Apa
- Vancouver
- BibTeX
- RIS
In: Organic letters, Vol. 22, No. 2, 17.01.2020, p. 675-678.
Research output: Contribution to journal › Article › Research › 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 -