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Total Synthesis and Structural Revision of Clavilactone D
Author(s) -
Takao Kenichi,
Nemoto Ryuichi,
Mori Kento,
Namba Ayumi,
Yoshida Keisuke,
Ogura Akihiro
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201700483
Subject(s) - butenolide , total synthesis , stereochemistry , ring closing metathesis , metathesis , ring (chemistry) , chemistry , organic chemistry , polymerization , polymer
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.