Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps

0489527 - ÚOCHB 2019 RIV GB eng J - Článek v odborném periodiku
Jagtap, Pratap - Císařová, I. - Jahn, Ullrich
Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps.
Organic & Biomolecular Chemistry. Roč. 16, č. 5 (2018), s. 750-755. ISSN 1477-0520. E-ISSN 1477-0539
Grant CEP: GA ČR GA203/09/1936
Institucionální podpora: RVO:61388963
Klíčová slova: isomerization * radicals * dimerization * lignans * electron transfer
Obor OECD: Organic chemistry
Impakt faktor: 3.490, rok: 2018
http://pubs.rsc.org/en/content/articlehtml/2018/ob/c7ob02848b

A very short three-step approach to trans, trans, trans-2,5-diaryl-3,4-dimethyltetrahydrofuran lignans is reported. The carbon skeleton is assembled in a single step based on an unprecedented tandem reaction consisting of 1,2-addition of aryllithium reagents to a, beta-unsaturated aldehydes, ruthenium-catalyzed redox isomerization of the resulting alkoxides to enolates and their dimerization triggered by single electron oxidation. The resulting 2,3-dialkyl-1,4-diketones form with moderate to good d/l-diastereoselectivity and are transformed to the target tetrahydrofuran lignans by reduction and diastereoselective cycloetherification.
Trvalý link: http://hdl.handle.net/11104/0283922