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DOI: 10.1055/s-0040-1719262
Synthesis of (±)-Leonuketal
Total Synthesis of (±)-Leonuketal.
Org. Lett. 2020;
22: 8735-8740
DOI: 10.1021/acs.orglett.0c03364.
Key words
(±)-leonuketal - 8,9-seco-labdane terpenoid - titanium catalysis - Shapiro reaction - fragmentation - gold catalysis - spiroketalizationSignificance
The tetracyclic 8,9-seco-labdane terpenoid (−)-leonuketal was isolated from the Chinese liverwort Leonurus japonicus and shows significant vasorelaxant activity against KCl-induced contraction of rat aorta. The authors present the first total synthesis relying on a Ti-mediated cyclization, a Shapiro reaction–fragmentation and an Au-catalyzed spirocyclization.
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Comment
Epoxide A was subjected to Ti-mediated radical cyclization to obtain bicyclic ketone B. Shapiro reaction–fragmentation was applied to furnish alkyne D. Alkylation of ketoester F with iodide E afforded alkyne G which was cyclized to butenolide H. Au-catalyzed spirocyclization delivered spiroketal I which was transformed into the natural product in additional 9 steps.
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Publikationsverlauf
Artikel online veröffentlicht:
16. Dezember 2020
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