THERMAL REARRANGEMENT OF TERT-BUTYL SUBSTITUTED 9,10- AND 11,12-ALLENIC RETINOIDS: 11 CIS-ISOMERS OF 19,19,19-AND 20,20,20-TRIMETHYLRETINOIDS

Article abstract of DOI:10.1016/S0040-4039(00)96243-9

The 9,10- and 11,12-allenic retinoids 5a and 6a, respectively, were synthesized in high yield and specificity by t-butylation of the propargylic benzoates 9b and 12b, respectively.Thermal isomerization of the allenes afforded the 11 cis, the 11,13-dicis, and the 9,11,13-tricis isomers of the 9-t-butyl retinol 3 and 11,13-dicis isomer of the 13-t-butyl retinol 4.