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Tetrahedron Lett. 2014 Jan 1;56(1):197-199.

Formal and total synthesis of (±)-cycloclavine.

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  • 1The University of Vermont, 82 University Place, Burlington, VT, 05405, United States.


A ring fragmentation and intramolecular azomethine ylide 1,3-dipolar cycloaddition sequence of reactions was successfully used in the preparation of a known (±)-cycloclavine precursor in good overall yield. Results of efforts to incorporate the tetrasubstituted cyclopropane ring present in cycloclavine are also discussed.


1,3-Dipolar Cycloaddition; Cycloclavine; Ergot Alkaloid; Natural Product Synthesis; Ring Fragmentation

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