Synfacts 2011(8): 0828-0828  
DOI: 10.1055/s-0030-1260850
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Sythesis of Serotonin Antagonists Using an Intramolecular Diels-Alder Approach

Contributor(s): Victor Snieckus, Matthew O. Kitching
S. Francis*, T. Kiyoi, M. Reid, K. Davies, S. Laats, D. McArthur, H. Feilden, A. M. Easson, Y. Kiyoi, G. Wishart, P. Ray
Merck Research Laboratories, Newhouse, UK
Further Information

Publication History

Publication Date:
20 July 2011 (online)


Reported is the stereoselective synthesis of tetrahydrobenzopyranopyrrolones (3 and 7) from the cyclobutenes 1 and 4 by an intramolecular hetero-Diels-Alder reaction under microwave irradiation conditions. The careful positioning of an auxiliary carbonyl functionality in the molecule allows the selective formation of the trans-fused ring system 6, or epimerization gives the more stable cis-fused ring system 2. The substrate scope of the process was not widely investigated.