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Enantioselective Synthesis of (-)-Roccellaric Acid

Böhm, Claudius ; Reiser, Oliver


A new strategy for the synthesis of anti-4,5-disubstituted -butyrolactones starting from inexpensive furan-2-carboxylic methyl ester was developed. By applying this methodology, the enantioselective synthesis of (-)-roccellaric acid ((-)-17) was accomplished using a copper(I)-catalyzed asymmetric cyclopropanation, a tin(IV)-catalyzed retroaldol/lactonization sequence of cyclopropanols, and a ruthenium-catalyzed intermolecular metathesis reaction as key steps.

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