Total Synthesis of TMC-95A

A Suzuki–Miyaura coupling reaction to form C1C20, macrolactamization at N9C10, and a mild decarboxylative anti elimination to selectively introduce the (Z)‐1‐propenylamide are key steps in a highly convergent and completely stereoselective synthesis of the potent proteasome inhibitor TMC‐95A (see...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2003-06, Vol.42 (23), p.2654-2657
Main Authors: Inoue, Masayuki, Sakazaki, Hayato, Furuyama, Hidetomo, Hirama, Masahiro
Format: Article
Language:English
Subjects:
biaryls
macrocycles
natural products
olefination
total synthesis
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Summary:A Suzuki–Miyaura coupling reaction to form C1C20, macrolactamization at N9C10, and a mild decarboxylative anti elimination to selectively introduce the (Z)‐1‐propenylamide are key steps in a highly convergent and completely stereoselective synthesis of the potent proteasome inhibitor TMC‐95A (see structure).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200351130