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

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...

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Bibliographic Details
Published inTetrahedron Vol. 165
Main Authors Shioda, Takayuki, Okamura, Hironori, Ogura, Yusuke, Takikawa, Hirosato
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 28.09.2024
Subjects
Artemisidiyne A
Cytotoxic compound
Polyacetylene
Sonogashira coupling
Structural revision
Sonogashira coupling
Cytotoxic compound
Artemisidiyne A
Structural revision
Polyacetylene
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Summary: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. [Display omitted] •Artemisidiyne A is a cytotoxic polyacetylene compound isolated from Artemisia lactiflora.•The first synthesis of artemisidiyne A has been achieved.•Artemisidiyne A was shown to be a trans-diol rather than the originally proposed cis-diol.•The absolute configuration of artemisidiyne A was determined to be 4R,5S.•Sequential Sonogashira-type cross-coupling was employed as the key reaction.
ISSN:0040-4020
DOI:10.1016/j.tet.2024.134190