A Compact Approach to an Isomeric Iheyamine A System and X-ray Crystal Structure of 5-Methyl-5H-azepino[2,3-b:4,5-b′]diindole

Abstract

A compact three-step synthesis of a new fused bisindole system isomeric with the heterocyclic skeleton present in the marine natural product iheyamine A has been achieved. The structure of the synthetic product was confirmed by a single-crystal X-ray structure.

Keywords:

• 5H-Azepino[2,3-b:4,5-b′]diindole
• Isomeric iheyamine A
• Rearrangement
• Spiro oxindoles

ACKNOWLEDGMENTS

We gratefully acknowledge the Royal Thai Government for a scholarship for W. S. and support from the University of Wollongong for this work. Use of the ChemMatCARS Sector 15 at the Advanced Photon Source, Chicago, USA, was supported by the Australian Synchrotron Research Program, which is funded by the Commonwealth of Australia under the Major National Research Facilities Program. ChemMatCARS Sector 15 is also supported by the National Science Foundation/Department of Energy under grant numbers CHE9522232 and CHE0087817 and by the Illinois Board of Higher Education. The Advanced Photon Source is supported by the U.S. Department of Energy, Basic Energy Sciences, Office of Science, under Contract No. W-31-109-Eng-38.