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email.gif - 0.3 KECHET96 Article 083: sglover
email.gif - 0.3 KRe: ECHET96 Article 083: greg tarrant

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

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

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.

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