Tetrahedron p. 6687 - 6692 (1986)
Update date:2022-08-05
Topics:
Gramatica
Manitto
Monti
Speranza
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.
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Doi:10.1021/jp983242i
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(2015)Doi:10.1039/b000318m
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(1998)