Abstract
AbstractNaturally occurring carbazole alkaloids including 2‐hydroxy‐3‐methylcarbazole, pyrano[3,2‐a]carbazole alkaloids (girinimbine and murrayacine) and prenylcarbazole alkaloids (mukoenine‐A and heptaphylline) have been synthesized on gram scale. The key compound in these syntheses is 9‐benzyl‐2‐methoxy‐3‐methylcarbazole, which was prepared by an efficient Au‐catalyzed cyclization reaction of readily available methoxypropadiene and indole‐2‐carbaldehyde. Girinimbine and murrayacine were synthesized by a concise PhB(OH)2‐mediated intermolecular cyclization with 3‐methylbut‐2‐enal. Palladium‐catalyzed allylation/Claisen rearrangement proved to be the best route to mukoenine‐A and heptaphylline.
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