Abstract
A formal synthesis of salinosporamide A is described. The tertiary alcohol function in salinosporamide A was stereoselectively generated via the substrate control by the reaction of a cyclic ketone derived from D-glucose with Me3Al, and subsequent Overman rearrangement of an allylic trichloroacetimidate effectively constructed the tetrasubstituted carbon with nitrogen. Formation of g-lactam, followed by the introduction of a cyclohexenyl unit furnished the Corey's intermediate of salinosporamide A.
| Original language | English |
|---|---|
| Pages (from-to) | 2983-2991 |
| Number of pages | 9 |
| Journal | Synthesis |
| Issue number | 17 |
| DOIs | |
| Publication status | Published - 2009 |
Keywords
- Carbohydrates
- Chiral pool
- Pericyclic reactions
- Rearrangements
- Stereoselective synthesis
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry