Work

Rapid Access to the Heterocyclic Core of the Calyciphylline A and Daphnicyclidin A-Type Daphniphyllum Alkaloids via Tandem Cyclization of a Neutral Aminyl Radical

Year: 2014

Type: article

Abstract: A streamlined approach to the tertiary amine-containing core of the calyciphylline A and daphnicyclidin A-type Daphniphyllum alkaloids is presented. A known carvone derivative is converted into the core structure in only four synthetic operations, and it is well poised for further elaboration. The key enabling methodology is a radical cyclization cascade beginning with addition of a secondary, neutral aminyl radical to the β-position of an enone, followed by trapping with a pendant alkyne.

Source: Organic Letters

DOI: 10.1021/ol4034868

Authors: Ahmad A. Ibrahim, Alexander N. Golonka, Alberto M. Lopez, Jennifer L. Stockdill

Institution: Wayne State University

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Wayne State University, National Institutes of Health, National Institute of General Medical Sciences