Organocatalyst-mediated five-pot synthesis of (-)-quinine.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 36477407.
- Also identified by DOI 10.1038/s41467-022-34916-z and PMC identifier 9729207.
- Licence recorded as CC BY.
- The licence permits redistribution, so the abstract is shown in full and the full text is available from the publisher.
Abstract
In this work, the enantioselective total synthesis of (-)-quinine has been accomplished in a pot-economical manner using five reaction vessels. In the first pot, reactions involve the diphenylprolinol silyl ether-mediated Michael reaction, aza-Henry reaction, hemiaminalization, and elimination of HNO<sub>2</sub> (five reactions), affording a chiral tetrahydropyridine with excellent enantioselectivity. In the second pot, five reactions proceed with excellent diastereoselectivity to afford a trisubstituted piperidine with the desired stereochemistry. A further five reactions are carried out in the last one-pot sequence.
Medical subject headings
- Quinine