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First Total Synthesis of Dihydroxerulin, a Potent Inhibitor of the Biosynthesis of Cholesterol
Author(s) -
Siegel Konrad,
Brückner Reinhard
Publication year - 1998
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19980615)4:6<1116::aid-chem1116>3.0.co;2-5
Subject(s) - biosynthesis , cholesterol , cholesterol synthesis , cholesterol lowering , chemistry , pharmacology , biochemistry , stereochemistry , medicine , gene , enzyme , reductase
Dihydroxerulin (5) is a noncytotoxic inhibitor of cholesterol biosynthesis . In spite of being achiral and devoid of OH groups, it was synthesized efficiently in 2×5 steps in two linear sequences plus one terminating step, from the optically active, multiply hydroxylated L ‐gulonolactone via the key intermediates 1 – 4 . 1 H NMR spectroscopy revealed that the C 8 =C 9 bond of synthetic and natural 5 is trans ‐substituted.