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Total Synthesis of Dinophysistoxin‐2 and 2‐ epi ‐Dinophysistoxin‐2 and Their PPase Inhibition
Author(s) -
Pang Yucheng,
Fang Chao,
Twiner Michael J.,
Miles Christopher O.,
Forsyth Craig J.
Publication year - 2011
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/anie.201101741
Subject(s) - biology , stereochemistry , alkene , botany , chemistry , biochemistry , catalysis
The first total syntheses of the title compounds highlight novel assemblies of the C1–C14 and C28–C38 domains, including an unexpected diastereoselectivity in the Sharpless asymmetric dihydroxylation of an alkene at C1C2. PPase inhibition assays revealed that 2‐ epi ‐DTX‐2 is at least 1 to 2 orders of magnitude less potent than DTX‐2, thus indicating that the configuration at C2 in DTX‐2 is crucial for potent inhibition (see picture).