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Synlett
DOI: 10.1055/a-2589-5573
DOI: 10.1055/a-2589-5573
letter
Semi-Synthesis of (+)-Digitoxigenin: Selective Bromination for Construction of the Key Intermediate
Supported by: Materia Medica First-Class Discipline of Nanjing University of Chinese Medicine ZYXJC2024-006Supported by: State Key Laboratory NZYSKL240204
Supported by: National Natural Science Foundation of China 82373710
Supported by: Key R&D Program of China 2023YFC2308200
A concise and scalable semi-synthesis of (+)-digitoxigenin (1) has been accomplished in 9 linear steps. This route features construction of the C(15)=C(16) double bond in intermediate 6 via selective C16 bromination followed by elimination. Subsequently, a single-step SeO2 oxidation directly installed the C14-β-hydroxyl group, producing 7. This strategy avoids precious metals, greatly reduces synthesis costs, and can be extended to the synthesis of related cardiotonic steroids.
Publication History
Received: 03 April 2025
Accepted after revision: 16 April 2025
Accepted Manuscript online:
16 April 2025
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