Issue 23, 1995

New, short synthesis of arylnaphthofuranone lignans based on reactions of o-aroylbenzyllithiums with furan-2(5H)-one

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 58 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 1316. The process proved to be applicable to the preparation of some 1-aryl type naphthofuranone lignans (collinusin, dehydrodimethylretrodendrin and justicidin B).

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1995, 3013-3016

New, short synthesis of arylnaphthofuranone lignans based on reactions of o-aroylbenzyllithiums with furan-2(5H)-one

K. Kobayashi, J. Tokimatsu, K. Maeda, O. Morikawa and H. Konishi, J. Chem. Soc., Perkin Trans. 1, 1995, 3013 DOI: 10.1039/P19950003013

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