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Chemie der Ginkgolide, VI. Herstellung von 1,10‐Dihydroxy‐ und 1,7,10‐Trihydroxyginkgolid aus 1,3,7,10‐Tetrahydroxyginkgolid
Author(s) -
Weinges Klaus,
Rümmler Matthias,
Schick Hartmut
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301162
Subject(s) - ginkgolides , chemistry , stereochemistry , yield (engineering) , ginkgo biloba , botany , materials science , metallurgy , biology
Chemistry of the Ginkgolides, VI. – Preparation of 1,10‐Dihydroxy‐ and 1,7,10‐Trihydroxyginkgolide from 1,3,7,10‐Tetrahydroxyginkgolide 1,3,7,10‐Tetrahydroxyginkgolide (“ginkgolide C”, 1 ) which can be isolated in large quantities from the terpene fraction of Ginkgo leaves, can be converted into 1‐( tert ‐butyldiphenylsilyloxy)‐3,7,10‐trihydroxyginkgolide ( 2 ) in 95% yield. 2 was converted via straightforward reactions into 1,7,10‐trihydroxyginkgolide (“ginkgolide M”, 9 ) and into the until now unknown 1,10‐dihydroxyginkgolide ( 15 ). 15 can also be obtained from 1,3,10‐trihydroxyginkgolide (“ginkgolide B”, 10 ). The intermediate products 14‐epiginkgolides 8 and 14 were epimerized to the ginkgolides with natural configuration at C‐14 by reaction with 4‐(dimethylamino)pyridine in acetonitrile. The title compounds are of interest for their possible activity as antagonists of the platelet activating factor (PAF).