Tetrahedron

The enantioselective synthesis of tetracyclic methyllycaconitine analogues

K Sparrow, D Barker, MA Brimble

Index: Sparrow, Kevin; Barker, David; Brimble, Margaret A. Tetrahedron, 2011 , vol. 67, # 41 p. 7989 - 7999

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Citation Number: 12

Abstract

A new enantioselective synthesis of ABEF ring analogues of methyllycaconitine has been developed using a chiral cobalt (III) salen-catalyzed Diels–Alder reaction to form the B ring. Subsequent elaboration to form the A, E and F rings was achieved by sequential Dieckmann, Mannich and Wacker-type cyclizations to afford tetracyclic analogues in 97.5% ee.

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