Synthesis and structural confirmation of artemisidiyne A, a cytotoxic compound isolated from the white mugwort, Artemisia lactiflora

Artemisidiyne A is a cytotoxic polyacetylene compound isolated from Artemisia lactiflora. The originally proposed structure was unprecedented, consisting of a cis-4,5-dihydroxy-2-cyclopentenone core with 1,3-pentadiynyl and 4-hydroxybutyl side chains. However, our synthesis of the proposed structure showed that it was partially incorrect, leading us to propose that the genuine artemisidiyne A might be a trans-diol rather than the reported cis-diol. Here, we report the synthesis of our proposed "trans-type" artemisidiyne A and demonstrate that it is identical to the natural product. 2009 Elsevier Ltd. All rights reserved.