Total Synthesis and Structural Revision of ClavilactoneD

A structural revision of clavilactoneD, a potent inhibitor of protein tyrosine kinases, was achieved by total syntheses of two newly proposed structures. The syntheses relied on ring-opening/ring-closing metathesis, which transformed a cyclobutenecarboxylate into a [gamma]-butenolide. The syntheses...

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Bibliographic Details
Published in:Chemistry : a European journal 2017-03, Vol.23 (16), p.3828-3831
Main Authors: Takao, Ken-ichi, Nemoto, Ryuichi, Mori, Kento, Namba, Ayumi, Yoshida, Keisuke, Ogura, Akihiro
Format: Article
Language:English
Subjects:
Chemistry
Decomposition reactions
Inhibitors
Kinases
Metathesis
Proteins
Synthesis
Tyrosine
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Summary:A structural revision of clavilactoneD, a potent inhibitor of protein tyrosine kinases, was achieved by total syntheses of two newly proposed structures. The syntheses relied on ring-opening/ring-closing metathesis, which transformed a cyclobutenecarboxylate into a [gamma]-butenolide. The syntheses confirmed that the correct structure of clavilactoneD has an amino group at C-3 instead of a hydroxy group at C-2 in the originally proposed structure.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201700483