Abstract
A full account of the total syntheses of proteasome inhibitors TMC-95A and -B is provided. A key feature of the syntheses involved installation of a cis-propenylamide moiety by a thermal rearrangement of an α-silylallyl amide. The scope and mechanism of the enamide-forming reaction are discussed. Also provided are some preliminary results from SAR studies. It was found that simplified analogues can retain the full potency of proteasome inhibition.
Original language | English (US) |
---|---|
Pages (from-to) | 6347-6355 |
Number of pages | 9 |
Journal | Journal of the American Chemical Society |
Volume | 126 |
Issue number | 20 |
DOIs | |
State | Published - May 26 2004 |
Externally published | Yes |
ASJC Scopus subject areas
- Catalysis
- General Chemistry
- Biochemistry
- Colloid and Surface Chemistry