A Simple Conversion of 2-Methoxynaphthoguinones to 2,3,4,5-Tetrahydronaphthofuran-4,5-diones. Application to the Synthesis of (+/-)-Trypethelones

DOI: 10.1021/jo00185a002

Source and publish data:

Journal of Organic Chemistry p. 1853 - 1857 (1984)

Update date:2022-08-04

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Authors:

Guay, Vincent

Brassard, Paul

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Article abstract of DOI:10.1021/jo00185a002

Structures proposed for trypethelone, O-methyltrypethelone, and O-methyl-8-methoxytrypethelone have been confirmed by synthesis.The required naphthoquinone substrates were prepared regiospecifically in one step by using vinylogous ketene acetals and then converted to the desired products essentially in a novel one-flask procedure.

Full text of DOI:10.1021/jo00185a002

Products guided by the article

Product name:(+/-)-2,3,4,5-Tetrahydro-7-methoxy-2,2,3,9-tetramethylnaphtho<1,2-b>furan-4,5-dione <(+/-)-β-Isotrypethelone methyl ether>

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