Concise access to primin, miconidin and related natural resorcinols

0478862 - ÚEB 2018 RIV GB eng J - Journal Article
Šíša, Miroslav - Dvořáková, Marcela - Vaněk, Tomáš
Concise access to primin, miconidin and related natural resorcinols.
Tetrahedron. Roč. 73, č. 35 (2017), s. 5297-5301. ISSN 0040-4020. E-ISSN 1464-5416
R&D Projects: GA MŠMT(CZ) LD15006
Institutional support: RVO:61389030
Keywords : Cross-coupling * Natural products * Primin * Qionones * Resorcinols
OECD category: Organic chemistry
Impact factor: 2.377, year: 2017

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.
Permanent Link: http://hdl.handle.net/11104/0274905