Total Synthesis of Applanatumol B

  • Author: Kristin Leyerer
  • Published: 09 July 2019
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Organic Letters/American Chemical Society
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Total Synthesis of Applanatumol B

The natural products applanatumol A and B were isolated from the fungus Ganoderma applanatum in 2016 [1]. Applanatumol B (pictured) features a dioxacyclopenta[cd]indene motif and five stereogenic centers. It shows biological activity against renal fibrosis, i.e., a kidney-related disease, and could, thus, be of interest in drug design.


Hisanaka Ito, Tokyo University of Pharmacy and Life Sciences, Japan, and colleagues have performed a total synthesis of applanatumol B. They used dimethoxybenzaldehyde and 4-pentyn-1-ol as starting materials. Key steps of the synthesis involved an intramolecular Morita-Baylis-Hillman reaction for a carbon–carbon bond formation between an aldehyde and an alkene moiety, a stereoselective Michael addition, and the stereoselective formation of the tricyclic structure. An intermediate with methylated aromatic hydroxy groups was obtained as a diastereomeric mixture in a ratio of 3:1 and 88 % yield. Its conversion to a quinone allowed separation of the diastereomers via HPLC, and a reductive aromatization gave the desired product, applanatumol B.


According to the researchers, this is the first successful total synthesis of applanatumol B. The final product was obtained in 14 steps.


 

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