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Preparation of selectively deuterated d‐γ‐tocotrienol
Author(s) -
Hyatt John A.,
Phillips Melissa
Publication year - 1999
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(19991230)42:13<1245::aid-jlcr280>3.0.co;2-c
Subject(s) - chemistry , tocotrienol , degree of unsaturation , halogenation , stereochemistry , tocopherol , natural product , antioxidant , organic chemistry , derivative (finance) , vitamin e , financial economics , economics
The naturally occurring hypocholesterolemic and antioxidant agent d‐γ‐tocotrienol ((2 R ), 3′‐ trans , 7′‐ trans ‐tocotrienol) differs from the related tocopherols (Vitamin E) by possessing isoprenoid side‐chain unsaturation. The presence of this unsaturation severely limits the chemistry available for tagging the substance. We were able to synthesize d‐γ‐tocotrienol‐5‐ 2 H from the natural product by selective bromination (NSB in CS 2 ) followed by transfer reduction using hydrazine‐d 4 catalysed by Pd/C. Copyright © 1999 John Wiley & Sons, Ltd.