Chemoenzymatic formal synthesis of (−)- and (+)-epibatidine
✍ Scribed by Boyd, Derek R.; Sharma, Narain D.; Kaik, Magdalena; McIntyre, Peter B. A.; Stevenson, Paul J.; Allen, Christopher C. R.
- Book ID
- 111687611
- Publisher
- Royal Society of Chemistry
- Year
- 2012
- Tongue
- English
- Weight
- 171 KB
- Volume
- 10
- Category
- Article
- ISSN
- 1477-0520
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Brominalion and bromoh)drox)lalion of oxazolidinones derived from cyclohexadienc have been studied in order to synlhctizc (\_+)-cpibatidine 18. Bromohydrox.wlation of compound 2 led to a polyfunctionalized halohydrin lla ~vhich could be furlher c.vclized to azabieyclol2.2. I Iheptan-2one 16 already
A total synthesis of racemic epibatidine, a natural product with analgesic activity, is described. Distinctly different from the previously published routes it starts from simple, known alkaloid in six steps.