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Lactone-directed intramolecular Diels-Alder cyclization: synthesis of trans-dihydroconfertifolin
Douglass F Taber1, Katsumasa Nakajima, Ming Xu
1Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
The Journal of Organic Chemistry
|June 22, 2002
Abstract:
Trienes 1 and 3 were obtained in five steps from ethyl 4-acetoxy-3-oxobutanoate and 6-iodo-3-methyl-1,3-hexadiene. Intramolecular Diels-Alder cyclization of 1 and 3 gave tricyclic lactones 2 and 4 as the major products, respectively. The key intermediate 4 was converted in two steps to trans-dihydroconfertifolin (5).