Abstract
The Ferrier carbocyclization reaction is one of the most powerful transformations of carbohydrates. This reaction provides enantiomerically pure cyclohexanone derivatives from aldohexoses, and is particularly useful in the chiral pool synthesis of cyclohexane-containing natural products from carbohydrates. We have investigated the synthesis of natural products utilizing the Ferrier carbocyclization reaction. This account provides a brief overview of the Ferrier carbocyclization and its application to natural product synthesis. The utility and versatility of the Ferrier carbocyclization reaction are showcased with the syntheses of hygromycin A, lycoricidine, actinobolin, galanthamine, and morphine starting from carbohydrates.
| Original language | English |
|---|---|
| Pages (from-to) | 592-605 |
| Number of pages | 14 |
| Journal | Chemical record (New York, N.Y.) |
| Volume | 14 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 2014 Aug 1 |
Keywords
- Ferrier carbocyclization reaction
- carbohydrates
- chiral pool
- natural products
- total synthesis
ASJC Scopus subject areas
- Chemistry(all)
- Biochemistry
- Chemical Engineering(all)
- Materials Chemistry