The tandem radical route to indole alkaloids: an unusual rearrangement reaction

Christopher A Ramsden,Stephen T Hilton,Keith Jones

doi:10.3998/ark.5550190.0008.b11

Abstract

Cyclisation of the precursor 6 under standard radical conditions yields the tetracyclic structure 7 which represents the core of a number of indole alkaloids along with the novel tetracycle 13.

Highlights

The Strychnos and Aspidosperma alkaloids are structurally complex molecules that possess a range of biological activity and present a challenge to synthetic organic chemists
As part of our ongoing interest in these classes of alkaloids,2 we are concerned with a synthesis of the core tetracyclic sub-structure 1, which forms the basis of these molecules as exemplified by strychnine 2 and aspidospermidine 3 (Figure 1)
We embarked on a synthesis of a cyclisation precursor which, after cyclisation, would enable us to access suitable intermediates for the synthesis of these two classes of alkaloids

Summary

Introduction

The Strychnos and Aspidosperma alkaloids are structurally complex molecules that possess a range of biological activity and present a challenge to synthetic organic chemists.1 As part of our ongoing interest in these classes of alkaloids,2 we are concerned with a synthesis of the core tetracyclic sub-structure 1, which forms the basis of these molecules as exemplified by strychnine 2 and aspidospermidine 3 (Figure 1).

Results

Conclusion