The synthesis of highly functionalised dienes for natural product synthesis

Authors
Parsons, PJ Gold, H Semple, G Montagnon, T
Citation
Pj. Parsons et al., The synthesis of highly functionalised dienes for natural product synthesis, SYNLETT, (8), 2000, pp. 1184-1186
Citations number
6
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
8
Year of publication
2000
Pages
1184 - 1186
Database
ISI
SICI code
0936-5214(200008):8<1184:TSOHFD>2.0.ZU;2-#
Abstract
The Lewis acid and Bronsted acid mediated intramolecular cyclisation reacti ons of allenyl epoxides to 1,3-dienes are reported. Titanium(IV) chloride a nd 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 sev en membered ring 1,3-diene. Trimethyloxonium tetrafluoroborate gives a six membered permethylated diene.