ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
(2R, 4′R, 8′R)- and (2S, 4′R, 8′R)-α-tocopherol have been synthesized by WITTIG reaction of the two enantiomeric S-(+)- and R-(-)-6-acetoxy-Z-formyl-2,5,7, 8-tetramethyl-chromans (I) with (3R, 7R)-hexahydrofarnesyl-triphenylphosphonium bromide (II), followed by hydrogenation and hydrolysis. (2R, 4′R, 8′R)-α-tocopherol proved to be identical in every respect with natural so called d-α-tocopherol. Resolution of the chroman component was achieved via the diastereomeric quinine salts of 2-carboxyethynyl-6-hydroxy-2,5,7,8- tetramethyl-chroman (XVIII). followed by transformation of the enantiomers into S-(+)- and R-(-)-I, respectively.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19630460225
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