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The synthesis of racemic pilocarpine has been achieved in high overall yield. Two alternative approaches for the formation of the γ-butyrolactone ring are described: the first involves a palladium-catalysed carbonylation reaction of a homopropargylic alcohol, whereas the second involves the palladium-catalysed decarboxylation/carbonylation of a 1,3-dioxan-2-one. Subsequent hydrogenation of an α-ethylidene lactone introduces the C(3)-stereochemistry to give a mixture of pilocarpine and isopilocarpine, its C(3)-epimer, which are readily separable by recrystallisation of their hydrochloride or nitrate salts. A concise synthesis of racemic pilosinine is also disclosed (37% overall yield in six steps); this also represents an alternative, formal synthesis of racemic pilocarpine. © 2009 Elsevier Ltd. All rights reserved.

Original publication

DOI

10.1016/j.tetlet.2009.03.021

Type

Journal article

Journal

Tetrahedron Letters

Publication Date

01/07/2009

Volume

50

Pages

3509 - 3512