Total Synthesis of Plakilactones C, B and des-Hydroxyplakilactone B by the Oxidative Cleavage of Gracilioether Furanylidenes

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• 作者：Matthew D. Norris ; Michael V. Perkins
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：August 5, 2016
• 年：2016
• 卷：81
• 期：15
• 页码：6848-6854
• 全文大小：478K
• 年卷期：0
• ISSN：1520-6904

文摘

A chemoselective oxidative cleavage of synthetic gracilioether B, 11-epi-gracilioether C benzoate, and des-hydroxygracilioether C with pyridinium chlorochromate, which proceeds with loss of the furanyl acetate, has enabled total synthesis and stereochemical elucidation of the marine sponge metabolites (4R,6R)-plakilactone C, (4R,6R,9R)-plakilactone B, and (4R,6R)-des-hydroxyplakilactone B. des-Hydroxygracilioether C, the putative biosynthetic precursor to hippolachnin A, was also found to undergo a facile ene cyclization on treatment with SnCl<sub>4sub>.