Two independent syntheses of enantiomerically pure ( 3R, 7R) -3,7,11-tri-methyldodecan-1-ol (), 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.
New syntheses of optically active vitamin E side chain by chemicoenzymatic approach / P. Gramatica, P. Manitto, D. Monti, G. Speranza. - In: TETRAHEDRON. - ISSN 0040-4020. - 42:24(1986), pp. 6687-6692.
New syntheses of optically active vitamin E side chain by chemicoenzymatic approach
G. Speranza
1986
Abstract
Two independent syntheses of enantiomerically pure ( 3R, 7R) -3,7,11-tri-methyldodecan-1-ol (), 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.
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