ChemInform Abstract: Highly Z Selective Synthesis of Functionalized Monoterpenoids via N- Ylide (2,3)Sigmatropic Rearrangement and Its Application to 13-cis- Retinol

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.