Rapid entry to phenanthroindolizidine alkaloids via an acid-catalysed acyliminium ion-electrocyclization cascade

Author:

St. Pierre Max1ORCID,Kempthorne Christine J.2,Liscombe David K.2,McNulty James1ORCID

Affiliation:

1. Department of Chemistry & Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario L8S 4M1, Canada

2. Vineland Research and Innovation Centre, 4890 Victoria Ave North, Box 4000, Vineland Station, Ontario L0R 2E0, Canada

Abstract

A synthesis of phenanthroindolizidine alkaloids was achieved via an acid catalysed deprotection-condensation-electrocyclization cascade. This provided a concise synthesis of (±)-seco-antofine and (±)-septicine in 4 steps and with high overall yields.

Funder

Natural Sciences and Engineering Research Council of Canada

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

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