Abstract
Expeditious synthesis of (R)-bicalutamide (1), a synthetic antiandrogen, from enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether (4) was achieved. An engineered Bacillus subtilis epoxide hydrolase worked enantioselectively on the racemic epoxide (7) to provide the above starting material in highly enantiomerically enriched state.
| Original language | English |
|---|---|
| Pages (from-to) | 979-983 |
| Number of pages | 5 |
| Journal | Tetrahedron Letters |
| Volume | 48 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 2007 Feb 5 |
Keywords
- (R)-1-Benzyloxy-2-methylpropane-2,3-diol
- Bicalutamide
- Diol
- Epoxide hydrolase
- Kinetic resolution
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Cite this
Fujino, A., Asano, M., Yamaguchi, H., Shirasaka, N., Sakoda, A., Ikunaka, M., Obata, R., Nishiyama, S., & Sugai, T. (2007). Bacillus subtilis epoxide hydrolase-catalyzed preparation of enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether and its application to expeditious synthesis of (R)-bicalutamide. Tetrahedron Letters, 48(6), 979-983. https://doi.org/10.1016/j.tetlet.2006.12.011