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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Homo-Clavulyne: Evaluation of a One-Atom Ring Expansion Strategy to Stabilize the Nine-Membered Ring Enediyne
Lande Hu1, Myungeun Jeong1, Mohammad R Seyedsayamdost1
1Department of Chemistry, Princeton University, Princeton, New Jersey, United States.
Abstract:
Streptomyces clavuligerus biosynthesizes a nine-membered ring enediyne that spontaneously cycloaromatizes to a 1,4-benzenoid diradical enroute to the clavulynes. Since nature also produces several isolable and exceedingly cytotoxic metabolites featuring 10-membered ring enediynes, we reasoned that a ring-expanded "homo-clavulyne" enediyne might be accessible by the concepts and methods of organic synthesis, isolable, and useful as a new molecular warhead with therapeutic applications. The design of a 10-membered ring homo-clavulyne enediyne and our circumstantial evidence for its existence are described herein.
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