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Paper | Regular issue | Vol 60, No. 6, 2003, pp.1351-1358
Published online, 24th March, 2003
DOI: 10.3987/COM-03-9737
4-Hydroxycoumarin and Related Systems: Sitoselectivity of the Mitsunobu Reaction with Prenyl Alcohols

Giancarlo Cravotto,* Gian Mario Nano, Giovanni Palmisano,* and Silvia Tagliapietra

*Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, via P. Giuria 9, I-10125 Torino, Italy

Abstract

The Mitsunobu reaction leads to the formation of new C-C bonds between prenyl alcohols and 1,3-dicarbonyl compounds like 4-hydroxycoumarin or its nitrogen isoster. Buchapine was obtained through a one-pot procedure from 4-hydroxy-2-quinolone and dimethylallyl alcohol.