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Total Synthesis of the Marine Natural Product 7‐Deoxy‐okadaic Acid: A Potent Inhibitor of Serine/Threonine‐Specific Protein Phosphatases
Author(s) -
Dounay Amy B.,
Urbanek Rebecca A.,
Sabes Steven F.,
Forsyth Craig J.
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990802)38:15<2258::aid-anie2258>3.0.co;2-#
Subject(s) - okadaic acid , threonine , serine , chemistry , natural product , phosphatase , biochemistry , total synthesis , stereochemistry , phosphorylation
A small change to the structure of okadaic acid ( 1 ), the omission of the single hydroxy group at C7, facilitated substantially the first total synthesis of the derivative 7‐deoxyokadaic acid ( 2 ). The conformation of 2 is in agreement with that of 1 and this minimal structural variation has been reported previously to have little effect on the inhibitory activity towards the serine/threonine‐specific protein phosphatases PP‐1 and PP‐2A.