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- W2116989559 abstract "Abstract In this article, the total syntheses of antimalarial compound decursivine and its biologically inactive sibling serotobenine are presented. The biomimetic synthesis of (±)‐serotobenine was investigated first, but failed. During the subsequent investigation of other synthetic routes, we discovered a new cascade Witkop photocyclization/elimination/addition sequence, which enabled the expedient synthesis of not only racemic decursivine and serotobenine, but also enantiopure (+)‐ and (−)‐decursivine and a variety of their analogues. The present syntheses represent the shortest pathway for the total synthesis of decursivine and serotobenine to date. Moreover, the newly developed cascade sequence for the total synthesis of decursivine does not need any protecting steps. The scope and the reaction mechanism of the cascade sequence were also studied. A rational mechanism for the cascade sequence is proposed, which is consistent with the previous studies and our current experimental results." @default.
- W2116989559 created "2016-06-24" @default.
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- W2116989559 creator A5013587375 @default.
- W2116989559 creator A5052580182 @default.
- W2116989559 creator A5059443638 @default.
- W2116989559 date "2013-01-10" @default.
- W2116989559 modified "2023-10-18" @default.
- W2116989559 title "Total Synthesis of (+)- and (−)-Decursivine and (±)-Serotobenine through a Cascade Witkop Photocyclization/Elimination/Addition Sequence: Scope and Mechanistic Insights" @default.
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- W2116989559 doi "https://doi.org/10.1002/chem.201204137" @default.
- W2116989559 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23307282" @default.
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