Synthesis of the aziridinomitosene skeleton by intramolecular Michael addition of α-lithioaziridines: An aromatic route featuring deuterium as a removable blocking …
E Vedejs, JD Little
Index: Vedejs, Edwin; Little, Jeremy D. Journal of Organic Chemistry, 2004 , vol. 69, # 6 p. 1794 - 1799
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Citation Number: 28
Abstract
A convergent synthetic route to the 1, 2-aziridinopyrrolo (1, 2-a) indole 34 has been developed. Key features of this route include the deuterium kinetic isotope effect to block undesired indole lithiation during tin-lithium exchange from 27a to 30a, the intramolecular Michael addition to generate the enolate 31a, and conversion into 34 by trapping with phenylselenenyl chloride. Reductive cleavage of the N-trityl group in 34 allows access to ...
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