Synthesis of 1H-2,3-dihydropyrrolizine derivatives as precursors of bifunctional alkylating agents
Two 1H-2,3-dihydropyrrolizine derivatives bearing a nitro group at the 6 position have been synthesized and an improved method for nitrating pyrroles using potassium nitrate in trifluoroacetic acid was developed. An efficient, two-step synthesis of the butterfly pheromone, Danaidone, was also developed with an overall 33% yield.
Novel amine-catalysed hydroalkoxylation reactions of activated alkenes and alkynes
Substoichiometric loadings of DBU catalyse the efficient 1,4-addition of alcohols and non-nucleophilic amines such as pyrrole to activated alkenes; the application of this methodology in a one-pot synthesis of a natural product, and as a novel strategy for the synthesis of mono-protected 1,3-carbonyl compounds is reported.
Murtagh, Julie E.,McCooey, Seamus H.,Connon, Stephen J.
p. 227 - 229
(2007/10/03)
Synthesis of 2,3-Dihydro-7-methyl-1H-pyrrolizin-1-one, the Sex Pheromone Danaidone
Danaidone (4) can easily be obtained in high yields from ethyl 3-methyl-1H-pyrrole-2-carboxylate (1) via Dieckmann reaction of the N-propanoate derivative 2.
Roeder, Erhard,Wiedenfeld, Helmut,Bourauel, Thomas
p. 1708 - 1710
(2007/10/02)
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