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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Cyclic Allene Approach to the Manzamine Alkaloid Keramaphidin B
Milauni M Mehta1, Jordan A M Gonzalez1, James L Bachman1
1Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.
Abstract:
We report an approach to the core of the manzamine alkaloid keramaphidin B that relies on the strain-promoted cycloaddition of an azacyclic allene with a pyrone trapping partner. The cycloaddition is tolerant of nitrile and primary amide functional groups and can be complemented with a subsequent retro-Diels-Alder step. These efforts demonstrate that strained cyclic allenes can be used to build significant structural complexity and should encourage further studies of these fleeting intermediates.
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