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• W1986231617 endingPage "8010" @default.
• W1986231617 startingPage "8003" @default.
• W1986231617 abstract "A linear synthesis of the indole alkaloid (+/-)-akuammicine (2) was completed by a novel sequence of reactions requiring only 10 steps from commercially available starting materials. The approach features a tandem vinylogous Mannich addition and an intramolecular hetero Diels-Alder reaction to rapidly assemble the pentacyclic heteroyohimboid derivative 8 from the readily available hydrocarboline 6. Oxidation of the E ring of 8 gave the lactone 9 that was converted into deformylgeissoschizine (11). The subsequent elaboration of 11 into 2 was effected by a biomimetically patterned transformation that involved sequential oxidation and base-induced skeletal reorganization. A variation of these tactics was then applied to the synthesis of the C(18) hydroxylated akuammicine derivative 36. Because 36 had previously been converted into strychnine (1) in four steps, its preparation constitutes a concise, formal synthesis of this complex alkaloid." @default.
• W1986231617 created "2016-06-24" @default.
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• W1986231617 date "2001-07-31" @default.
• W1986231617 modified "2023-09-29" @default.
• W1986231617 title "Biogenetically Inspired Approach to the <i>Strychnos </i>Alkaloids. Concise Syntheses of (±)-Akuammicine and (±)-Strychnine" @default.
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• W1986231617 doi "https://doi.org/10.1021/ja010935v" @default.
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• W1986231617 hasPublicationYear "2001" @default.
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