New syntheses of optically active vitamin E side chain by chemicoenzymatic approach

Article abstract of DOI:10.1016/S0040-4020(01)82109-8

Two independent syntheses of enantiomerically pure ( 3R, 7R) -3,7,11-tri-methyldodecan-1-ol (2a), the C₁₅ tocopherol side chain, are described. Both reaction sequences start from (R)-citrohellol, obtained by baker's yeast reduction of geraniol. One strategy is based on the coupling between (R)-citronellyl bromide and a C₅ optically active unit derived from chemical degradation of the common starting template; the other one uses an achiral isoprenic unit and a C₁₀, building block containing two asymmetric carbon atoms generated by microbial reactions.