Synthesis of New Cantharimide Analogues Derived from 3-Sulfolene
SYNTHESIS-STUTTGART, sa.7, ss.1079-1084, 2011 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Basım Tarihi: 2011
- Doi Numarası: 10.1055/s-0030-1258466
- Dergi Adı: SYNTHESIS-STUTTGART
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.1079-1084
- Anahtar Kelimeler: ene reactions, epoxidation, photooxidations, halogenation, stereoselective synthesis, heterocycles
- Atatürk Üniversitesi Adresli: Evet
Özet
New types of norcantharimide analogues were prepared by three methods: epoxidation, photooxidation, and bromination. Epoxidation of deoxynorcantharimide with m-chloroperoxybenzoic acid gave an isomeric mixture. The selective formation of the synisomers was attributed to dipole-dipole interactions between the peracid and imide moiety. Photooxidation of deoxynorcanthamide gave syn- and anti- hydroperoxide analogues through ene addition of singlet oxygen; the anti-hydroperoxide was the major product in this case, as a result of the steric effect of the imide ring. Bromination of deoxynorcantharimide and subsequent transformations gave a pyrrolidine and the phthalimide core structure.