Support studies toward the hicksoane alkaloids reveal cascade reactions of a (tryptophanamido)methylglycinate
Literature Information
Stephanie Lee, Tilo Söhnel, Jonathan Sperry
Herein we report unanticipated results that emerged from a synthetic study targeting the unique triazocane present in the hicksoane alkaloids. An initial strategy focused on the cyclisation-ring expansion of a 3-(tryptophyl)imidazolidin-4-one failed due to the high reactivity of the imide unit; passing a methanolic solution of this compound through a weakly basic ion exchange resin led to methanolysis to form a (tryptophanamido)methylglycinate. Attempted lactamisation of this (tryptophanamido)methylglycinate led to the formation of a (tryptophyl)imidazolidin-4-one, a rare imidazopyrido[3,4-b]indolone and a β-carboline. Control reactions informed a mechanistic rationale for these cascade processes.
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Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
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