Chemoenzymatic Synthesis of (+)-Asperpentyn and the Enantiomer of the Structure Assigned to Aspergillusol A

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• 作者：Ping Lan ; Lauren E. White ; Ehab S. Taher ; Prudence E. Guest ; Martin G. Banwell ; Anthony C. Willis
• 刊名：Journal of Natural Products
• 出版年：2015
• 出版时间：August 28, 2015
• 年：2015
• 卷：78
• 期：8
• 页码：1963-1968
• 全文大小：318K
• ISSN：1520-6025

文摘

Total syntheses of (+)-asperpentyn (1) and compound ent-2, the enantiomer of the structure, 2, assigned to the natural product aspergillusol A are reported. Both reaction sequences employ the enzymatically derived and enantiomerically pure cis-1,2-dihydrocatechol 4 as starting material and use Sonogashira cross-coupling chemistry to install the required enyne side-chain. The ¹H and ¹³C NMR spectroscopic data derived from compound ent-2 match those reported for aspergillusol A, thus suggesting that the gross structure of this natural product has been assigned correctly, although its absolute stereochemistry remains unclear.