4.4 Article

Bio-inspired dimerisation of prenylated quinones directed towards the synthesis of the meroterpenoid natural products, the scabellones

期刊

TETRAHEDRON LETTERS
卷 56, 期 12, 页码 1486-1488

出版社

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.02.024

关键词

Meroterpenoid; Dimerisation; Bio-inspired; Marine natural product; Scabellone

资金

  1. University of Auckland

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Stirring 2-geranyl-6-methoxy-1,4-hydroquinone in pyridine/O-2 or 2-gerany1-6-methoxy-1,4-benzoquinone in pyridine/N-2 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. (C) 2015 Elsevier Ltd. All rights reserved.

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