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

• Main Authors: Lathrop, Stephen (Contributor), Kim, Justin (Contributor), Movassaghi, Mohammad (Contributor)
• Other Authors: Massachusetts Institute of Technology. Department of Chemistry (Contributor)
• Format: Article
• Language: English
• Published: Swiss Chemical Society, 2013-11-22T14:17:23Z.
• Subjects: Article
• Online Access: Get fulltext

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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.
National Institute of General Medical Sciences (U.S.) (GM089732)
Amgen Inc.
Camille & Henry Dreyfus Foundation