Tetrahedron

A practical and scaleable total synthesis of the jaborandi alkaloid (+)-pilocarpine

…, PM Roberts, PT Stephenson, HR Storr, JE Thomson

Index: Davies, Stephen G.; Roberts, Paul M.; Stephenson, Peter T.; Storr, Helen R.; Thomson, James E. Tetrahedron, 2009 , vol. 65, # 39 p. 8283 - 8296

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Citation Number: 15

Abstract

The total synthesis of (+)-pilocarpine (as its nitrate salt) has been achieved in nine steps and 30% overall yield starting from racemic 2-(2′, 2′-dimethoxyethyl) propane-1, 3-diol, which was desymmetrised via an enzymatic protocol. A high yielding synthesis of a key α- ethylidene lactone precursor has been developed, which involves the palladium-catalysed decarboxylation/carbonylation of a 1, 3-dioxan-2-one for formation of the γ-butyrolactone ...