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Facile Asymmetric Synthesis of the Core Nuclei of Xanthanolides, Guaianolides and Eudesmanolides

Nosse, Bernd ; Chhor, Rakeshwar B. ; Jeong, Won Boo ; Böhm, Claudius ; Reiser, Oliver


Bicyclic and tricyclic -butyrolactones with 5,7-, 5,6,5-, 5,6,6-, or 5,7,5-fused ring systems, being found in xanthanolides, eudesmanolides, and guaianolides, were readily synthesized from methyl furan-2-carboxylic acid. Key steps were a copper(I)-catalyzed asymmetric cyclopropanation, Sakurai allylations, intramolecular ene reactions, and ring-closing metathesis reactions.

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