A highly stereoselective total synthesis of (±)castanospermine
✍ Scribed by Jean-Louis Reymond; Pierre Vogel
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 174 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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## Abstract The total synthesis of (+)‐9‐__epi__‐dictyostatin (**1b**), a diastereomer of the antimitotic marine‐sponge‐derived macrolide (–)‐dictyostatin (**1a**), was achieved by creating 11 stereogenic centers and 4 stereogenic double bonds with a high level of stereocontrol. The yield for the 2
carried out by treating 5 with 1.4-dibromobutane in dimethylformamide (DHF) in the presence of potassium tert-butoxide to afford 6 in 39% yield. Then focus was turned to the synthesis of deoxysesbanine (12). On the contrary to the easy alkoxycarbonylation of 4, treatment of 7 under the same reaction