B. Schmidt, S. Audörsch
Stereoselective total syntheses of polyacetylene plant metabolites via ester-tethered ring closing metathesis
J. Org. Chem. 2017, 82, 1743-1760
DOI: 10.1021/acs.joc.6b02987
Total syntheses of five naturally occurring polyacetylenes from three different plants are described. These natural products have an E,Z-configured conjugated diene linked to a di- or triyne chain in common. As the key method to stereoselectively establish the E,Z-diene part, an ester-tethered ring-closing metathesis/base-induced eliminative ring opening sequence was used. The results presented herein do not only showcase the utility of this tethered RCM variant, but have also prompted us to suggest that the originally assigned absolute configurations of chiral polyacetylenes from Atractylodes macrocephala should be revised or at least reconsidered.
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