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Rh-Catalyzed Hydroformylation-Initiated Bicyclization: Construction of Azabicyclic Systems.

ABSTRACT: Here, we describe the recent progress toward construction of 1-azabicyclic structures using a domino hydroformylation double cyclization strategy of an amide bearing the trisubstituted alkene functionality. The method provides a rapid and atom-economic access to alkaloid structures under mild conditions, especially for quinolizidine and pyrrolidine-fused azepane skeletons with yields up to 82% and good diastereoselectivity. Subsequent oxidative cleavage conditions are developed for the synthesis of Dendrobatid alkaloid epi-epiquinamide.

SUBMITTER: Chiou WH

PROVIDER: S-EPMC7045571 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Rh-Catalyzed Hydroformylation-Initiated Bicyclization: Construction of Azabicyclic Systems.

Chiou Wen-Hua WH Hsu Kuo-Hsun KH Huang Wen-Wei WW

ACS omega 20200212 7

Here, we describe the recent progress toward construction of 1-azabicyclic structures using a domino hydroformylation double cyclization strategy of an amide bearing the trisubstituted alkene functionality. The method provides a rapid and atom-economic access to alkaloid structures under mild conditions, especially for quinolizidine and pyrrolidine-fused azepane skeletons with yields up to 82% and good diastereoselectivity. Subsequent oxidative cleavage conditions are developed for the synthesis ...[more]

PMID: 32118187

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