Highly Z selective synthesis of functionalized monoterpenoids via N-ylide [2,3]sigmatropic rearrangement and its application to 13-cis-retinol

Article abstract of DOI:10.1246/cl.1996.671

Highly stereoselective elongation of a functionalized E isoprene unit on the Z terminal methyl of prenol was achieved by the N-ylide rearrangement of N-tiglyl-β-methallyldimethyl-ammonium salt. (E,Z)-Rearrangement product was converted into 13-cis-retinol via useful conjugated triene isoprenoid synthon.