New, short synthesis of arylnaphthofuranone lignans based on reactions of o-aroylbenzyllithiums with furan-2(5H)-one
- 1 January 1995
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 23,p. 3013-3016
- https://doi.org/10.1039/p19950003013
Abstract
A simple and general method to prepare 9-arylnaphtho[2,3-c]furan-1(3H)-one derivatives has been developed. The reaction of o-aroylbenzyllithiums with furan-2(5H)-one gave the corresponding adducts 5–8 and 5′–7′, which upon treatment with thionyl chloride in pyridine followed by dehydrogenation with Pd–C in refluxing p-cymene afforded the arylnaphthofuranone derivatives 13–16. The process proved to be applicable to the preparation of some 1-aryl type naphthofuranone lignans (collinusin, dehydrodimethylretrodendrin and justicidin B).Keywords
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