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Synthesis 2011(7): 1079-1084  
DOI: 10.1055/s-0030-1258466
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of New Cantharimide Analogues Derived from 3-Sulfolene

Ayse Tan, Birgul Koc, Ertan Sahin, Nurhan H. Kishali*, Yunus Kara*
Department of Chemistry, Faculty of Sciences, Atatürk University, 25240 Erzurum, Turkey
Fax: +90(0442)2360948; e-Mail: yukara@atauni.edu.tr; e-Mail: nhorasan@atauni.edu.tr;
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Publication History

Received 13 December 2010
Publication Date:
08 March 2011 (online)

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Abstract

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 syn-isomers 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.

Key words

ene reactions - epoxidation - photooxidations - halogenation - stereoselective synthesis - heterocycles

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1

Author to whom inquires concerning the X-ray structure should be directed. E-mail: ertan@atauni.edu.tr.