1. The Synthesis of Highly Functionalised Dienes for Natural Product Synthesis
- Author
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Tamsyn Montagnon, Helen Gold, Philip J. Parsons, and Graeme Semple
- Subjects
Diene ,Chemistry ,Allene ,Organic Chemistry ,Ring (chemistry) ,Chloride ,Medicinal chemistry ,chemistry.chemical_compound ,Hydrofluoric acid ,medicine ,Trimethyloxonium tetrafluoroborate ,Lewis acids and bases ,Brønsted–Lowry acid–base theory ,medicine.drug - Abstract
The Lewis acid and Bronsted acid mediated intramolecular cyclisation reactions of allenyl epoxides to 1,3-dienes are reported. Titanium(IV) chloride and hydrofluoric acid give six membered carbocyclic dienes, whereas stannic chloride affords a 2:1 mixture of six and seven membered rings respectively. Diethylaluminum chloride mediated cyclisation furnishes exclusively a seven membered ring 1,3-diene. Trimethyloxonium tetrafluoroborate gives a six membered permethylated diene.
- Published
- 2000
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