Affiliation:
1. Institut für Organische Chemie Karlsruher Institut für Technologie (KIT) Kaiserstraße 12 76131 Karlsruhe Germany
Abstract
AbstractRoutes to the framework of perylenequinone‐derived mycotoxins of the biphenyl type are described. 1,2,11,12‐Tetrahydroperylenequinone is most suitably prepared in seven steps starting with 3‐hydroxyacetophenone. Key steps are an Ullmann coupling, pinacol‐type cyclization, bromination, enolate reaction, and intramolecular Friedel‐Crafts cyclization. A second approach starting with 1,5‐dihydroxynaphthalene yields the respective decarbonylated core. Key steps of this 5‐step sequence are again an Ullmann coupling and a McMurry olefination. The cleavage of the preferentially utilized hexyl protecting group could be achieved with boron bromide.
Funder
Deutsche Forschungsgemeinschaft
Subject
Organic Chemistry,Physical and Theoretical Chemistry