Radical-mediated Dimerization and Oxidation Reactions for the Synthesis of Complex Alkaloids

Authors

  • Stephen P. Lathrop
  • Justin Kim
  • Mohammad Movassaghi Massachusetts Institute of Technology, Departement of Chemistry, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA

DOI:

https://doi.org/10.2533/chimia.2012.389

Keywords:

Alkaloid, Diazene fragmentation, Hexahydropyrroloindole, Radical dimerization, Radical oxidation

Abstract

Concise and general strategies for radical-based dimerization of cyclotryptamine and cyclotryptophan derivatives in addition to radical-based oxidation of structurally complex diketopiperazines are discussed. The impact of these radical-based chemistries on the rapid generation of molecular complexity is highlighted using representative examples from recent complex homodimeric alkaloid total syntheses. Additionally, a new and general strategy for radical-based directed heterodimerization of cyclotryptamine substructures via solvent-caged unsymmetrical diazene fragmentation is discussed.

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Published

2012-06-27

How to Cite

[1]
S. P. Lathrop, J. Kim, M. Movassaghi, Chimia 2012, 66, 389, DOI: 10.2533/chimia.2012.389.

Issue

Section

Scientific Articles