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Diastereoselective synthesis of fluoroisosteric analogues of antiparasitic pyrrolobenzoxazine alkaloids from tryptophan by successive fluorination–cyclization and a Meisenheimer-type rearrangement

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Abstract

Fluoroisosteric analogues of an antiparasitic pyrrolobenzoxazine alkaloid CJ-12663 were designed and diastereoselectively synthesized by successive fluorination–cyclization and a Meisenheimer-type rearrangement from tryptophan in good yields.

Graphical abstract: Diastereoselective synthesis of fluoroisosteric analogues of antiparasitic pyrrolobenzoxazine alkaloids from tryptophan by successive fluorination–cyclization and a Meisenheimer-type rearrangement

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Publication details

The article was received on 25 Mar 2017, accepted on 22 May 2017 and first published on 23 May 2017


Article type: Research Article
DOI: 10.1039/C7QO00234C
Citation: Org. Chem. Front., 2017, Advance Article
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    Diastereoselective synthesis of fluoroisosteric analogues of antiparasitic pyrrolobenzoxazine alkaloids from tryptophan by successive fluorination–cyclization and a Meisenheimer-type rearrangement

    B. K. Das, E. Tokunaga, K. Harada, Y. Sumii and N. Shibata, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00234C

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