Chemoenzymatic synthesis of both enantiomers of alpha-tocotrienol.
The stereoselective acylation of the achiral chromanedimethanol derivative 1 by vinyl acetate in the presence of Candida antarctica lipase B gave the (S)-monoester 2 in high enantiomeric purity (ee > or = 98%). Enzymatic hydrolysis of diesters of compound 1 failed to give (R)-monoester 2 in good yield and high ee. Thus, both enantiomers of alpha-tocotrienol were synthesized from the (S)-monoester 2.
Chênevert
Robert
R
Département de chimie, faculté des sciences et de génie, Université Laval, Québec, Canada G1K 7P4. robert.chenevert@chm.ulaval.ca
Courchesne
Gabriel
G
Pelchat
Nicholas
N
D000215:Acylation; D002175:Candida / Q000201:enzymology*; D004952:Esters / Q000737:chemistry; D005656:Fungal Proteins; D006868:Hydrolysis; D008049:Lipase / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D024508:Tocotrienols; D014810:Vitamin E / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D004952:Esters; D005656:Fungal Proteins; D024508:Tocotrienols; D014810:Vitamin E; C082032:tocotrienol, alpha; D008049:Lipase; C431349:lipase B, Candida antarctica