Tetrahedron letters

A new synthetic method for allene-1, 3-dicarboxylates using DMC and a novel tandem cyclization to a pyrrolizidine alkaloid skeleton

M Node, T Fujiwara, S Ichihashi, K Nishide

文献索引：Node, Manabu; Fujiwara, Toshio; Ichihashi, Shogo; Nishide, Kiyoharu Tetrahedron Letters, 1998 , vol. 39, # 35 p. 6331 - 6334

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被引用次数: 26

摘要

A new one-step synthesis of allene-1, 3-dicarboxylates from acetone-1, 3-dicarboxylates in high yields was developed by the use of DMC as a dehydrating reagent. This process opened a new expeditious route to a 1-azabicyclo [3.3. 0] octane skeleton of pyrrolizidine alkaloids from dimethyl acetone-1, 3-dicarboxylate and bis (2-chloroethyl) amine via a Michael addition and a novel tandem cyclization.