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Total Synthesis of (±)-Impatien A via Aza-Heck Cyclization.

ABSTRACT: The first total synthesis of the natural product impatien A is described. This concise synthesis features an aza-Heck cyclization to construct the complex spirocyclic ring system and provides a rare example of the use of aza-Heck cyclizations in complex molecule synthesis. To enable this key cyclization of an electrophilic nitrogen atom with a tetrasubstituted alkene, we utilized high-throughput experimentation to identify a new ligand and ultimately deliver impatien A in seven steps from known compounds.

SUBMITTER: Korch KM 

PROVIDER: S-EPMC8454492 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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Total Synthesis of (±)-Impatien A via Aza-Heck Cyclization.

Korch Katerina M KM   Watson Donald A DA  

Organic letters 20210830 18

The first total synthesis of the natural product impatien A is described. This concise synthesis features an aza-Heck cyclization to construct the complex spirocyclic ring system and provides a rare example of the use of aza-Heck cyclizations in complex molecule synthesis. To enable this key cyclization of an electrophilic nitrogen atom with a tetrasubstituted alkene, we utilized high-throughput experimentation to identify a new ligand and ultimately deliver impatien A in seven steps from known  ...[more]

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