Synthesis of Clionamine B, an Autophagy Stimulating Aminosteroid Isolated from the Sponge Cliona celata

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• 作者：Roberto Forestieri ; Elizabeth Donohue ; Aruna Balgi ; Michel Roberge ; Raymond J. Andersen
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：August 2, 2013
• 年：2013
• 卷：15
• 期：15
• 页码：3918-3921
• 全文大小：290K
• 年卷期：v.15,no.15(August 2, 2013)
• ISSN：1523-7052

文摘

Clionamine B (2), an aminosteroid isolated from the marine sponge Cliona celata, has been synthesized starting from the plant sapogenin tigogenin (5). A key step in the synsthesis is the stereoselective introduction of the C-20 伪-hydroxyl substituent via oxidation of a 纬-lactone enolate with molecular oxygen. Synthetic clionamine B (2) strongly stimulated autophagy in human breast cancer MCF-7 cells.