Journal
TETRAHEDRON LETTERS
Volume 46, Issue 21, Pages 3623-3627Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.03.175
Keywords
resolvins; hydrolytic kinetic resolution; palladium catalyst; Takai reaction; Lindlar reduction
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The first total synthesis of 7(S),17(S)-Resolvin D5, a lipid mediator derived from docosahexacnoic acid, has been achieved. The chiral centers were generated via a Co-salen hydrolytic kinetic resolution of a terminal epoxide with > 99% ee. Key steps include Takai olefination, Pd-0/Cu-I coupling and simultaneous deprotection and ester cleavage with lipase from Candida rugosa. (c) 2005 Elsevier Ltd. All rights reserved.
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