Synthesis and Determination of Absolute Configuration of 伪-Pyrones Isolated from Penicillium corylophilum

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• 作者：J. S. Yadav ; B. Ganganna ; Palash Dutta ; Kiran K Singarapu
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：November 21, 2014
• 年：2014
• 卷：79
• 期：22
• 页码：10762-10771
• 全文大小：502K
• ISSN：1520-6904

文摘

The first total synthesis of (S)-6-(2,9-dihydroxynonyl)-4-hydroxy-3-methyl-2H-pyran-2-one, 4-hydroxy-3-methyl-6-((2S,4R)-2,4,11-trihydroxyundecyl)-2H-pyran-2-one, and its unnatural 2R,4R-isomer starting from commercially available 1,8-octanediol is described. The synthesis led to the revision of the proposed structural assignment of the natural product as (R)-6-(2,9-dihydroxynonyl)-4-hydroxy-3-methyl-2H-pyran-2-one. The key steps include chiral auxiliary mediated asymmetric acetate aldol reaction, dianion addition, and base mediated cyclization to form an 伪-pyrone ring.