Work

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

Year: 2012

Type: review

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.

Source: CHIMIA International Journal for Chemistry

DOI: 10.2533/chimia.2012.389

Authors: Stephen P. Lathrop, Justin Kim, Mohammad Movassaghi

Institution: Massachusetts Institute of Technology

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: Amgen, National Institutes of Health, National Institute of General Medical Sciences

Awards: Synthesis and Study of Cyclotryptamine and Diketopiperazine Alkaloids, G843036647