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Stereoselective, Multicomponent Approach to Quaternary Substituted Hydroindole Scaffolds.

ABSTRACT: The Amaryllidaceae alkaloids have been a target of synthesis for decades due to their complex architectures and biological activity. A central feature of these natural product cores is a quaternary substituted hydroindole heterocycle. Building off the foundation of our previous multicomponent approach to highly functionalized pyrrolidinones, herein we report a highly convergent, diastereoselective, multicomponent approach to access the hydroindole cores present within crinine, haemanthamine, pretazettine, and various other bioactive alkaloids. These scaffolds are additionally useful as building blocks for druglike molecules and natural product like library generation.

SUBMITTER: Massaro NP

PROVIDER: S-EPMC7662074 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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Stereoselective, Multicomponent Approach to Quaternary Substituted Hydroindole Scaffolds.

Massaro Nicholas P NP Pierce Joshua G JG

Organic letters 20200617 13

The Amaryllidaceae alkaloids have been a target of synthesis for decades due to their complex architectures and biological activity. A central feature of these natural product cores is a quaternary substituted hydroindole heterocycle. Building off the foundation of our previous multicomponent approach to highly functionalized pyrrolidinones, herein we report a highly convergent, diastereoselective, multicomponent approach to access the hydroindole cores present within crinine, haemanthamine, pre ...[more]

PMID: 32610919

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