1384289-51-3Relevant articles and documents
A tandem Diels-Alder/Mannich approach to the synthesis of AE and ABE ring analogues of Delphinium alkaloids
Goodall, Kirsten J.,Brimble, Margaret A.,Barker, David
, p. 5759 - 5778 (2012)
The one-pot TiCl4 catalysed Diels-Alder/Mannich reaction of α-cyanoaminoacrylates with 2-silyloxy-1,4-butadienes gives 6-keto-3-azabicyclo[3.3.1]nonane-1-carboxylates. Reduction of the ketone and alkylation of the resultant alcohol gives 6-alkoxy-3-azabicyclo[3.3.1]nonanes mimicking the AE rings of a number of Delphinium and Aconitum alkaloids, with the same stereochemistry as the natural products.