Abstract
The stereoselective total synthesis of (+)-galanthamine (+)-1 starting from d-glucose is described. The cyclohexene ring in (+)-1 was prepared in an optically active form from d-glucose using Ferrier's carbocyclization reaction, and the critical quaternary carbon was stereoselectively generated via chirality transfer based on the Claisen rearrangement of a cyclohexenol. The dibenzofuran skeleton was effectively constructed by the bromonium ion-mediated intramolecular cyclization of a cyclohexene possessing a phenolic ether function. After the introduction of a carbon-carbon double bond, the Pictet-Spengler type cyclization, followed by the reduction of the amide function completed the chiral synthesis of (+)-1.
Original language | English |
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Pages (from-to) | 6267-6270 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 48 |
Issue number | 36 |
DOIs | |
Publication status | Published - 2007 Sept 3 |
Externally published | Yes |
Keywords
- Chiral synthesis
- Claisen rearrangement
- Galanthamine
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry