Benzaldehyde → 1H-​Inden-​3-​ol

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Reaction Steps

Alternatively, compounds of formula I can be prepared as shown in Scheme 10. A benzaldehyde derivative 7-1 can be alkylated by treatment with n-butyllithium in the presence of N,N,N′-trimethylethane-1,2-diaminene followed by quenching with acrolein. The resulting semiacetal 10-1 can be converted to an olefin by treating with Ph3PCH3Br/n-butyllithium. Cyclization using Grubbs catalyst gives rise to 3-hydroxyindene derivative 10-3 which can be subjected to an oxidation using an oxidant such as pyridinium chlorochromate (PCC). Michael addition of intermediate 8-5 to the resulting ketone 10-4 affords intermediate 10-5. Following reduction of the ketone to alcohol, alkylation with R9I can be accomplished using a base such as sodium hydride. Removal of Boc followed by coupling with R1CO2H using a coupling agent such as EDCI/HOBt affords compounds of formula 10-7.

Provenance & Evidence