Synlett 2017; 28(01): 1-11
DOI: 10.1055/s-0036-1588372
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© Georg Thieme Verlag Stuttgart · New York

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

Robert B. Susick, Lucas A. Morrill, Elias Picazo, Neil K. Garg*
  • Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095, USA   Email: neilgarg@chem.ucla.edu
Further Information

Publication History

Received: 17 November 2016

Accepted: 21 November 2016

Publication Date:
08 December 2016 (eFirst)

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