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Hydrindanone Synthesis: An Incisterol Model

✍ Scribed by Massimo Curini; Francesco Epifano; Maria C. Marcotullio; Ornelio Rosati; Ming Guo; Yousheng Guan; Ernest Wenkert

Publisher
John Wiley and Sons
Year
2005
Tongue
German
Weight
111 KB
Volume
88
Category
Article
ISSN
0018-019X

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✦ Synopsis

Ethyl 1-methyl-2-oxocyclohexanecarboxylate (1a) and its homologue 1b were converted to hydroisobenzofuran acids 7 (via 6-[(butylsulfanyl)methylene] and epoxide derivatives), one of which furnished hexalone derivative 11 (via an intermediate diazomethyl ketone derivative). The above-mentioned starting esters were converted to ethylene ketals, the free-radical oxidations of which led to hydrobenzofuran acids. One of the latter led to a hydrindanone (via a diazomethyl ketone), whose further chemical elaboration yielded an incisterol model. A second hydrobenzofuran acid gave a cyclobutenone (via the diazomethyl ketone), which was transformed into a more-stable cyclopentenone isomer by treatment with Lewis acid.

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