Scalable total synthesis of horsfiequinone A. Issue 15 (11th April 2018)

• Record Type: Journal Article
• Authors: Zhan, Rui; Du, Shou-Zhen; Kuang, Fang; Chen, Ye-Gao
• Is Part Of: Tetrahedron letters. Volume 59:Issue 15(2018)
• Page Start: 1451
• Page End: 1453
• Publication Date: 2018-04-11
• Subjects: Diarylpropane -- Horsfiequinone A -- 1, 4-p-Benzoquinone -- Scalable synthesis -- Diarylpropane dimer; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.02.082
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A four-step total synthesis of horsfiequinone A. Gram-scale synthesis. Only one column chromatography purification is needed. Abstract: Starting from two commercially available substrates, methoxyhydroquinone and piperonyl alcohol, a scalable four-step total synthesis of horsfiequinone A was developed. The notable feature of the synthesis is the application of two continuous sequential transformations. Namely, the key aldehyde9 and horsfiequinone A were prepared via scalable Wittig/hydrolysis and Wittig/catalytic hydrogenation/oxidation sequences, respectively. Importantly, the synthetic route required only three recrystallizations and one column chromatography purification step.