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Stereocontrolled Total Synthesis of (5 S ,6 R )‐, (5 S ,6 S )‐, (5 R ,6 R )‐, and (5 R ,6 S )(7 E ,9 E ,11 Z ,14 Z )‐5,6‐Dihydroxy‐7,9,11,14‐icosatetraenoic Acid (5,6‐DiHETE) Methyl Esters
Author(s) -
Nicolaou K. C.,
Ramphal J. Y.,
Palazon J. M.,
Spanevello R. A.
Publication year - 1989
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.198905871
Subject(s) - diastereomer , enantiomer , stereochemistry , metabolite , chemistry , arachidonic acid , total synthesis , biological activity , organic chemistry , biochemistry , enzyme , in vitro
The (5 S , 6 R )‐configurated title compound 1 is of interest as a biologically active metabolite of arachidonic acid. A method for the synthesis of 1 which also can be extended to the enantiomer and the two diastereomers now makes these compounds readily accessible in amounts satisfactory enough for biological experiments.