(HMe₂SiCH₂)₂: A Useful Reagent for B(C₆F₅)₃-Catalyzed Reduction-Lactonization of Keto Acids: Concise Syntheses of (-)-cis-Whisky and (-)-cis-Cognac Lactones

Hengmu Xie, Ji Lu, Yingying Gui, Lu Gao, Zhenlei Song*

*Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P. R. of China, Email: zhenleisongscu.edu.cn

H. Xie, J. Lu, Y. Gui, L. Gao, Z. Song, Synlett, 2017, 28, 2453-2459.

DOI: 10.1055/s-0036-1588488

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Abstract

(HMe₂SiCH₂)₂ is a useful reagent for a reductive, B(C₆F₅)₃-catalyzed lactonization of keto acids to provide γ- and δ-lactones. The process enables the synthesis of (-)-cis-whisky and (-)-cis-cognac lactones in good overall yields.

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Key Words

lactonization, reduction, silanes, B(C₆F₅)₃, keto acids

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ID: J60-Y2017