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Synfacts 2005(0): 0021-0021  
DOI: 10.1055/s-2005-865375
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Radical-Mediated Synthesis of Sesquiterpene Lactones

Contributor(s): Victor Snieckus, Zhongdong Zhao
E. Jezek, A. Schall, P. Kreitmeier, O. Resier*
University of Regensburg, Germany
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Publication History

Publication Date:
20 July 2005 (online)

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Significance

Starting from inexpensive methyl 2-furoate, via the intermediate cyclopentenylbutenolide (4 steps, 26% overall yield), bi- and tricyclic g-butyrolactone cores can be formed stereoselectively and in good yields via Y-substituent - directed radical cyclization. Using R = Br, CN, CO2Et, COMe substitution, reactions proceed in acceptable yields.