Host: Division of Organic Chemistry, The Pharmaceutical Society of Japan
Pages 62-63
As an extension of our study on the sysnthesis of retinoic acid analogs, we developed a novel synthesis of analogs containing the ring systems such as indene, benzofurane and indole in place of 2,6,6-trimethylcyclohexene ring including 7–8 double bond in retinoic acid. Enol triflates derived from 2-indanone, 2-chromanone and N-methyl oxindole are smoothly reacted with E- and Z-3-tributylstannyl-2-butenols in the presence of a palladium catalysis to afford the corresponding coupling products. 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.
