エノールノナフラートのカップリング反応を利用したレチノイン酸アナログの合成

抄録

As an extension of our study on the stereoselective synthesis of retinoic acid analogs, we developed a novel synthesis of analogs having the different substituted moiety on the cyclohexene ring in retinoic acid. Enol nonaflates derived from various cylohexene-1-yl-acetaldehyde are smoothly reacted with E- and Z-3-tributylstannyl-2-butenols in the presence of the palladium catalyst to afford the corresponding coupling products in good to excellent yields. After oxidation with MnO₂, the resulting aldehydes were converted into the retinoic acid analogs via Emmons–Horner reaction of C5 phosphonate and subsequent basic hydrolysis.

Scheme 1