Application of the Meisenheimer rearrangement to the synthesis of hydroxylated tropane alkaloid derivatives

John B. Bremner^a, Reginald J. Smith^b and Gregory J. Tarrant^a

^aDepartment of Chemistry, University of Wollongong, NSW, Australia, 2522
^bPhytex Australia Pty Ltd, Sydney, NSW, Australia

Introduction

Recently, there has been considerable interest shown in the newly discovered polyhydroxylated nortropane alkaloids known as the calystegins¹. Along with physoperuvine² and 1-hydroxytropacocaine³ they are the only known nortropane and tropane alkaloids to possess a hemiaminal functionality.

Project aim

Our aim was to investigate a Meisenheimer rearrangement approach to the basic bridgehead hydroxylated skeleton present in these alkaloids based on an advanced alkaloid starting material. Herein, we report a racemic synthesis of a 3-a-hydroxy analogue of physoperuvine, in which the tropane ring was derived from scopolamine.

Synthetic strategy

Results, page 2

Application of the Meisenheimer rearrangement to the synthesis of hydroxylated tropane alkaloid derivatives

John B. Bremnera, Reginald J. Smithb and Gregory J. Tarranta

Introduction

Project aim

Synthetic strategy

John B. Bremner^a, Reginald J. Smith^b and Gregory J. Tarrant^a