2002/12/01 by Stephen M. Lynch, Scott K. Bur, Albert Padwa · 2 citations
Chemistry · #Asymmetric Synthesis and Catalysis #Synthesis and Reactivity of Heterocycles #Organic Chemistry Cycloaddition Reactions
paper · doi:10.1021/ol027024q
openalex publication_date 2002/12/01 · openalex created_date 2016/06/24 · openalex updated_date 2026/08/01
[reaction: see text] The intramolecular Diels-Alder reaction between an amidofuran moiety tethered onto an indole component was examined as a strategy for the synthesis of Aspidosperma and Strychnos alkaloids. Furanyl carbamate 13 was acylated using the mixed anhydride 16 to provide amidofuran 12 in 68% yield. Further N-acylation of this indole furnished 17 in 88% yield. Cyclization precursors were prepared by removing the carbamate moiety followed by N-alkylation with the appropriate alkyl halides. Thermolysis of 25 provided the novel tetracyclic ketone 26 in 74% yield.