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Communication | Regular issue | Vol 60, No. 1, 2003, pp.23-27
Published online, 25th November, 2002
DOI: 10.3987/COM-02-9640
One-Pot Synthesis of Macrocyclic Dioxatetralactones from the Sequential Inter- and Intramolecular [2+2] Photocycloaddition Reactions

Tetsuro Shimo, Makoto Kawamura, Eriko Fukushima, Mikio Yasutake, Teruo Shinmyozu, and Kenichi Somekawa*

*Kagoshima University, Faculty of Engineering, Department of Applied Chemistry, Korimoto, Kagoshima 890, Japan


Sensitized photocycloaddition reactions of polymethylenedioxy-di-2-
pyrones (1 - 3) with ethylene diacrylate (4a) afforded macrocyclic dioxatetralactones (6a - 8a) having sixteen- to eighteen-membered rings. Similar reaction of 1 with ethylene dimethacrylate (4b) afforded similar lactones (6b) and (9). The stereochemical features of 6a and 7a depending on the chain length elucidated by the X-Ray crystal analysis are figured by MOPAC conformational analysis of the reactants (1, 2 and 4a).