- A MICROBIAL LIPASE BASED STEREOSELECTIVE SYNTHESIS OF (d)-α-TOCOPHEROL FROM (R)-CITRONELLAL AND (S)-(6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-YL)ACETIC ACID
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A new sythesis of natural vitamin E (2R,4'R,8'R)-α-tocopherol) based on (R)-citronellal and (S)-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)acetic acid is described.The citronellal is elaborated into an optically pure C13 allylic carbonate using a lipase catalyzed kinetic resolution to control the new chiral center.Palladium catalyzed coupling of the C13 carbonate with either a β-ketoester or β-ketosulphone derived from the chromanylacetic completes the assembly of the α-tocopherol skeleton.Appropriate functional group modifications are used to complete the synthesis.
- Coffen, David L.,Cohen, Noal,Pico, Anthony M.,Schmid, Rudolph,Sebastian, Mark J.,Wong, Frederick
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p. 527 - 552
(2007/10/02)
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- 2-(trimethyl-tridecenyl)-tetramethylchroman intermediates for vitamin E
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6-Etherified hydroxy -2-(4',8',12'-trimethyl-5'-tridecenyl)-2,5,7,8-tetramethylchromans with an oxo or hydroxy substituent at the 2' position which may be substituted with an arylsulfonyl or a carboxyalkyl at the 3' position and containing a single or double bond at the 11 position, said chromans being intermediates for producing natural vitamin E.
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