A concise one-step synthesis of primin and iso-primin. Issue 17 (22nd April 2015)

• Record Type: Journal Article
• Authors: Nasiri, Hamid R.; Ferner, Jan; Tükek, Caner; Krishnathas, Robin; Schwalbe, Harald
• Is Part Of: Tetrahedron letters. Volume 56:Issue 17(2015)
• Page Start: 2231
• Page End: 2233
• Publication Date: 2015-04-22
• Subjects: Primin -- Quinones -- 1, 1-ADEQUATE -- Radical allylation -- C–H functionalization of quinones; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.03.073
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A short, efficient one-step synthesis of primin and its isomer is devised. The synthesis is based on the introduction of an alkyl side chain via radical alkylation of 2-methoxy-benzoquinone. The required alkyl radical was either generated from the corresponding alkyl acid or alkyl boronic acid in the presence of persulfate under silver catalysis. The alkylation of 2-methoxy-benzoquinone occurs at the C-6 and C-5 position, generating the desired primin and iso-primin. The formation of the natural product primin was confirmed by NMR spectroscopy determining carbon–carbon constitution at 13 C natural abundance in an 1, 1-ADEQUATE experiment.