First syntheses of 2,2-dimethyl-7-(2'-methylbut-3'-en-2'-yl)-2H-chromen-6-ol and 2-(3'-methylbut-2'-enyl)-5-(2'-methylbut-3'-en-2'-yl)-1,4-benzoquinone, novel prenylated quinone derivatives from the New Zealand brown alga Perithalia capillaris.
The first syntheses of 2,2-dimethyl-7-(2'-methylbut-3'-en-2'-yl)-2H-chromen-6-ol (1) and 2-(3'-methylbut-2'-enyl)-5-(2'-methylbut-3'-en-2'-yl)-1,4-benzoquinone (2), novel prenylated quinone derivatives from the New Zealand brown alga Perithalia capillaris, are reported, in which the key steps are consecutive Claisen rearrangements that proceed with both high chemo- and regioselectivity.
Coombes
Catherine L
CL
School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom.
Moody
Christopher J
CJ
D000475:Alkenes / Q000737:chemistry*; D016227:Benzoquinones / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008745:Methylation; D008956:Models, Chemical; D000459:Phaeophyceae / Q000737:chemistry*; D054876:Prenylation; D011809:Quinones / Q000737:chemistry*
D000475:Alkenes; D016227:Benzoquinones; D007202:Indicators and Reagents; D011809:Quinones