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