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DOI: 10.1039/A804365E (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 3267-3276

The synthesis of various cycloalkana[d[hair space]]xanthones and conversion of the cyclohexa-analogue to a 7,7a-dimethylcyclohexa[d[hair space]]xanthene[hair space]†

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Roy M. Letcher, Tai-Yuen Yue, Kwei-Fung Chiu, Avijit S. Kelkar and Kung-Kai Cheung

Abstract

The synthesis of cyclo-penta-, -hexa- and -hepta-[d[hair space]]xanthones 5 from (E[hair space])-(2-hydroxyphenyl)-5-arylpent-4-ene-1,3-diones 4, cycloalkanones and pyrrolidine is described. Reactions to modify 5 in an attempt to synthesize analogues of the five naturally occurring cyclohexa[d[hair space]]xanthenes (with general formula 1) are also described: these reactions include C-methylations at C-7 and C-7a, hydride reduction of the 8-keto group, dehydroxylations and finally catalytic reduction to give 16. The stereochemistry of 16 established by NOE and an X-ray crystal structure of 9aB differs from 1 at two contiguous C-atoms.

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