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

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.

SUBMITTER: Terunuma T

PROVIDER: S-EPMC9729207 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

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

Terunuma Takahiro T Hayashi Yujiro Y

Nature communications 20221207 1

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 trisu ...[more]

PMID: 36477407

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