177327-03-6Relevant articles and documents
Bio-inspired dimerisation of prenylated quinones directed towards the synthesis of the meroterpenoid natural products, the scabellones
Chan, Susanna T.S.,Pullar, Michael A.,Khalil, Iman M.,Allouche, Emmanuelle,Barker, David,Copp, Brent R.
, p. 1486 - 1488 (2015)
Stirring 2-geranyl-6-methoxy-1,4-hydroquinone in pyridine/O2 or 2-geranyl-6-methoxy-1,4-benzoquinone in pyridine/N2 affords the dimeric meroterpenoid natural products, scabellones A-C in modest to low yields and also identifies 2-methoxy-6-(4-methylpent-3-en-1-yl)-1,4-naphthoquinone (scabellone E) as a new natural product. The corresponding reaction of the des-methoxy analogue, 2-geranyl-1,4-benzoquinone in degassed pyridine for three days afforded the natural product cordiachromene A (15% yield) and 6-(4-methylpent-3-en-1-yl)-1,4-naphthoquinone (12%), the latter being a likely biosynthetic precursor to the marine meroterpenoid alkaloids, conicaquinones A and B.