Organocatalyst-mediated five-pot synthesis of (–)-quinine

Takahiro Terunuma and Yujiro Hayashi ()
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Takahiro Terunuma: Tohoku University
Yujiro Hayashi: Tohoku University

Nature Communications, 2022, vol. 13, issue 1, 1-7

Abstract: 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 HNO2 (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.

Date: 2022
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DOI: 10.1038/s41467-022-34916-z

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