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.
Hydrindanone Synthesis: An Incisterol Model
CURINI, Massimo;MARCOTULLIO, Maria Carla;ROSATI, Ornelio;
2005
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
