Concise access to primin, miconidin and related natural resorcinols. Issue 35 (31st August 2017)

• Record Type: Journal Article
• Authors: Sisa, Miroslav; Dvorakova, Marcela; Vanek, Tomas
• Is Part Of: Tetrahedron. Volume 73:Issue 35(2017)
• Page Start: 5297
• Page End: 5301
• Publication Date: 2017-08-31
• Subjects: Primin -- Qionones -- Resorcinols -- Cross-coupling -- Natural products; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.07.029
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: An efficient and short synthetic procedures affording the biologically active natural products primin, miconidin, olivetol, grevillol, and cardol (adipostatin A) in high yields are reported. The two strategies involve Sonogashira and Suzuki cross-couplings as the crucial steps for the installation of the alkyl side-chains. Syntheses start from cheap, commercially available 1-bromo-3, 5-dimethoxybenezene to obtain 1, 3-dimethoxy-5-(alk-1-yn-1-yl)benzene as the key intermediate. This intermediate can be easily and economically oxidized to provide primin in excellent overall yield while avoiding undesired side products by the virtue of its symmetry. The demethylation of the key intermediate affords natural resorcinols olivetol, grevillol, and cardol, respectively. The reduction of primin provides its hydroquinone derivative miconidin. Graphical abstract: