Cookies on this website

We use cookies to ensure that we give you the best experience on our website. If you click 'Accept all cookies' we'll assume that you are happy to receive all cookies and you won't see this message again. If you click 'Reject all non-essential cookies' only necessary cookies providing core functionality such as security, network management, and accessibility will be enabled. Click 'Find out more' for information on how to change your cookie settings.

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




Journal article


Tetrahedron Letters

Publication Date





3509 - 3512