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Stereoselective synthesis of the imidazole alkaloids (+)‐pilocarpine and (+)‐isopilocarpine. (Imidazole chemistry, Part IX)

1981; Royal Netherlands Chemical Society; Volume: 100; Issue: 12 Linguagem: Inglês

10.1002/recl.19811001202

1878-7096

A. Noordam, L. Maat, H. C. Beyerman,

Axial and Atropisomeric Chirality Synthesis

Abstract A novel synthesis of (+)‐pilocarpine ( 10a ) is described. L‐Histidine is converted into methyl (R)‐2‐bromo‐3‐(l‐methyl‐5‐imidazolyl)propionate ( 5 ) in which the configuration has been inverted. Alkylation of dibenzyl ethylmalonate with 5 yields the imidazole compound 6 , again with inversion. Finally, 6 is converted into a mixture of (+)‐pilocarpine ( 10a ) and (+)‐isopilocarpine ( 10b ), the separation of which is well established.