Journal
TETRAHEDRON LETTERS
Volume 43, Issue 20, Pages 3719-3722Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(02)00606-8
Keywords
cyclopropanes; immunosuppressive compounds; marine metabolites; sphingolipids; sponges; stereochemistry
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The absolute configuration of plakoside A {(2S,3R,11R*,12S*)-2-[(2'''R,5'''Z,11'''R*,12'''S*)-2'''-hydroxy-11''',12'''-methylene-5'-docosenamido]-1-O-[2'-O-(3''-methyl-2-butenyl)-beta-D-galactopyranosyl]-11,12-methylene-1,3-docosanediol} was determined as 11S,12R,11'''S,12'''R by its degradation to two cyclopropane-containing fatty acids followed by their derivatization with a chiral reagent and subsequent HPLC analysis of the resulting derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.
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