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) |
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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