Total Synthesis and Structural Revision of Clavilactone D

A structural revision of clavilactone D, 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 γ‐butenolide. The syntheses confi...

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Veröffentlicht in:Chemistry : a European journal 2017-03, Vol.23 (16), p.3828-3831
Hauptverfasser: Takao, Ken‐ichi, Nemoto, Ryuichi, Mori, Kento, Namba, Ayumi, Yoshida, Keisuke, Ogura, Akihiro
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Sprache:eng
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Zusammenfassung:A structural revision of clavilactone D, 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 γ‐butenolide. The syntheses confirmed that the correct structure of clavilactone D has an amino group at C‐3 instead of a hydroxy group at C‐2 in the originally proposed structure. Easy D: A structural revision of clavilactone D 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 γ‐butenolide. The correct structure of clavilactone D 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