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- W2953257788 abstract "Development of efficient sequences for the total syntheses of (±)-actinophyllic acid (rac-1) and (−)-actinophyllic acid (1) are described. The central step in these syntheses is the aza-Cope/Mannich reaction, which constructs the previously unknown hexacyclic ring system of actinophyllic acid in one step from much simpler tetracyclic precursors. The tetracyclic hexahydro-1,5-methano-1H-azocino[4,3-b]indole ketone rac-37 is assembled from o-nitrophenylacetic acid in four steps, with oxidative cyclization of a dienolate derivative of tricyclic precursor rac-35 being the central step. In the first-generation synthesis, this intermediate is transformed in two steps to homoallyl amine rac-43, whose formaldiminium derivative undergoes efficient aza-Cope/Mannich reaction to give pentacyclic ketone rac-44. In four additional steps, this intermediate is advanced to (±)-actinophyllic acid. The synthesis is streamlined by elaborating ketone rac-37 to β-hydroxyester intermediate rac-53, which is directly transformed ..." @default.
- W2953257788 created "2019-06-27" @default.
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- W2953257788 date "2010-07-09" @default.
- W2953257788 modified "2023-09-26" @default.
- W2953257788 title "ChemInform Abstract: Total Synthesis of (.+-.)- and (-)-Actinophyllic Acid." @default.
- W2953257788 cites W2064967571 @default.
- W2953257788 doi "https://doi.org/10.1002/chin.201031204" @default.
- W2953257788 hasPublicationYear "2010" @default.
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