Total Synthesis and Structural Revision of Clavilactone D | Zendy

Takao Kenichi | Zendy; Nemoto Ryuichi | Zendy; Mori Kento | Zendy; Namba Ayumi | Zendy; Yoshida Keisuke | Zendy; Ogura Akihiro | Zendy

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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.

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