Microwave-mediated Claisen rearrangement followed by phenol oxidation: A simple route to naturally occurring 1, 4-benzoquinones. The first syntheses of …

…, TE Hurst, AM Jacob, CJ Moody

Index: Davis, Christopher J.; Hurst, Timothy E.; Jacob, Aouregan M.; Moody, Christopher J. Journal of Organic Chemistry, 2005 , vol. 70, # 11 p. 4414 - 4422

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Citation Number: 53

Abstract

The naturally occurring 1, 4-benzoquinones 2-methoxy-6-propyl-1, 4-benzoquinone (1), 2- methoxy-6-pentyl-1, 4-benzoquinone (primin 2), 2-methoxy-6-pentadecyl-1, 4- benzoquinone (3), 2-methoxy-6-heptadecyl-1, 4-benzoquinone (dihydroirisquinone, pallasone B; 4) were synthesized by a simple protocol involving microwave accelerated Claisen rearrangement of allyl ethers 10, followed by hydrogenation of the side chain ...