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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Facile and rapid route for the synthesis of novel conformationally constrained norstatine analogs via
Arthur Y Shaw1, Federico Medda, Christopher Hulme
1Department of Pharmacology and Toxicology, College of Pharmacy, BIO5 Oro Valley, 1580 E. Hanley Blvd, The University of Arizona, Tucson, AZ.
Abstract:
The following report describes novel methodology for the rapid synthesis of unique conformationally constrained norstatine analogs of potential biological relevance. A PADAM (Passerini reaction - Amine Deprotection - Acyl Migration reaction) sequence is followed by a TFA-mediated microwave-assisted cyclization to generate the final benzimidazole isostere of the norstatine scaffold in moderate to good yields. The applicability of this solution phase methodology to the preparation of a small collection of compounds is discussed.
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