Issue 9, 2017

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
25 Mar 2017
Accepted
22 May 2017
First published
23 May 2017

Org. Chem. Front., 2017,4, 1726-1730

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, 4, 1726 DOI: 10.1039/C7QO00234C

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