Synthesis of oxepanes and trans-fused bisoxepanes via biomimetic, endo-regioselective tandem oxacyclizations of polyepoxides

Authors
McDonald, FE Wang, X Do, B Hardcastle, KI
Citation
Fe. Mcdonald et al., Synthesis of oxepanes and trans-fused bisoxepanes via biomimetic, endo-regioselective tandem oxacyclizations of polyepoxides, ORG LETT, 2(18), 2000, pp. 2917-2919
Citations number
39
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
18
Year of publication
2000
Pages
2917 - 2919
Database
ISI
SICI code
1523-7060(20000907)2:18<2917:SOOATB>2.0.ZU;2-4
Abstract
This communication describes the first examples of tandem endo-regioselecti ve and stereospecific oxacyclizations of 1,5-diepoxides to oxepane products and a similar tandem oxacyclization of 1,5,9-triepoxides to fused bisoxepa ne cyclic carbonates. A mechanism for these biomimetic oxacyclizations is p roposed in which the epoxides act as both electrophilic and nucleophilic re action partners.