Intramolecular Amidofuran Cycloadditions across an Indole π-Bond: An Efficient Approach to theAspidospermaandStrychnosABCECore
Authors:
- 1 December 2002
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (26) , 4643-4645
Abstract
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.Keywords
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