Pardon the Interruption: A Modification of Fischer’s Venerable ­Reaction for the Synthesis of Heterocycles and Natural Products

^‡ These authors contributed equally.

Abstract

This account provides an overview of our laboratory’s studies of an unusual variant of the Fischer indolization reaction. We describe the discovery of the so-called ‘interrupted Fischer indolization’ and the development of the reaction from a methodological standpoint. In addition, our efforts to evaluate and apply this methodology in the context of akuammiline alkaloid total synthesis are discussed.

1 Introduction

2 Interrupted Fischer Indolization Methodology

3 Applications in Akuammiline Alkaloid Total Synthesis

4 Concluding Thoughts

Key words

total synthesis - alkaloids - heterocycles - natural products - akuammilines - indolines - indoles - Fischer indolization

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