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- Title
Novel synthesis of a highly functionalized cyclopropane derivative.
- Authors
Trudeau, Stéphane; Deslongchamps, Pierre
- Abstract
A model study was carried out to explore the feasibility of synthesizing fused tricyclic ring structures containing a C7—C8 double bond juncture (steroid numbering) by employing an SN2' cyclization of a silyl enol ether to displace an allylic acetate as the key step. Instead of the anticipated product, highly functionalized cyclopropanes were obtained. These novel cyclopropane structures are the result of the concomitant 1,2-migration of a dithiane thioether moiety and the eventual displacement of the acetate group, followed by the cyclization of the silyl enol ether.
- Subjects
CYCLOPROPANE; PROPANE; RING formation (Chemistry); CHEMISTRY
- Publication
Canadian Journal of Chemistry, 2003, Vol 81, Issue 9, p1003
- ISSN
0008-4042
- Publication type
Article
- DOI
10.1139/v03-119