Abstract
An efficient, highly stereocontrolled total synthesis of trichostatin A (1) has been achieved in 9 steps with 17.4% overall yield and >99% optical purity from readily available achiral starting materials. The key features of this synthesis include the L-proline-promoted, highly enantioselective cross-aldol reaction as a crucial step for the construction of the C-6 chiral center and the minimization of racemization by final step oxidation of the OH group to a ketone at position 7.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1228-1234 |
| Number of pages | 7 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 348 |
| Issue number | 10-11 |
| DOIs | |
| State | Published - Jul 2006 |
| Externally published | Yes |
Keywords
- Aldol reaction
- Asymmetric organocatalysis
- HDAC inhibitors
- Proline
- Trichostatin A
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry