Stereoselectivity in the organoiron-mediated synthesis of (±)-mesembrine
- Resource Type
- Article
- Authors
- Roe, Caroline; Sandoe, Elizabeth J.; Stephenson, G. Richard; Anson, Christopher E.
- Source
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Jan2008, Vol. 49 Issue 4, p650-653. 4p.
- Subject
- *ENANTIOMERS
*CHIRALITY
*CHEMICAL reactions
*TETRAHEDRA
- Language
- ISSN
- 0040-4039
Abstract: The preparation and structural characterisation of a 1-aryl-substituted electrophilic η5-cyclohexadienyliron complex with the correct functionalisation as a ‘C12 building block’ for the synthesis of (±)-mesembrine establishes the accessibility of a flattened conformation to allow nucleophile addition ipso to the arene. The chirality relay in quaternary centre formation by nucleophile addition has been confirmed, and the product has been converted into the Sceletium alkaloid mesembrine. [Copyright &y& Elsevier]