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Paper | Regular issue | Vol 60, No. 8, 2003, pp.1865-1872
Published online, 23rd June, 2003
DOI: 10.3987/COM-03-9812
Synthesis of (±)-Rolipram

Meng-Yang Chang,* Pei-Pei Sun, Shui-Tein Chen,* and Nein-Chen Chang*

*Institute of Biological Chemistry, Academia Sinica, 128, Yan-Chiu-Yuan Road, Sec II, NanKang, Taipei, 11529, Taiwan, R.O.C.

Abstract

A facile synthesis of rolipram via stepwise [3+2] annulation and desulfonated hydrolysis was reported. Base-induced coupling/cyclization reactions of α-sulfonylacetamide with (Z)-2-bromoacrylic ester yielded three contiguous centers on the pyroglutamate system with trans-trans orientation as the one-pot key step.