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Stereocontrolled Total Synthesis of Lipoxins As and B 5
Author(s) -
Nicolaou K. C.,
Webber S. E.,
Ramphal J.,
Abe Y.
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198710191
Subject(s) - total synthesis , halide , yield (engineering) , chemistry , organic chemistry , catalysis , combinatorial chemistry , stereochemistry , materials science , metallurgy
Icosapentaenoic acids and their metabolites are of both nutritional and bio‐medical interest. The title compounds were previously accessible in only very small amounts via biosynthetic routes. Their first total synthesis has now been achieved in good yield and in a stereocontrolled fashion. The key steps were a Pd 0 –Cu 1 ‐catalyzed coupling of terminal alkynes with vinyl halides to give the icosanoid skeleton and Lindlar hydrogenation to give the Z olefins.