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Intramolecular amidofuran cycloadditions across an indole pi-bond: an efficient approach to the aspidosperma and
Stephen M Lynch1, Scott K Bur, Albert Padwa
1Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Organic Letters
|December 20, 2002
Abstract:
[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.