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

Biplab Kumar Das; Etsuko Tokunaga; Kyosuke Harada; Yuji Sumii; Norio Shibata

doi:10.1039/C7QO00234C

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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

Biplab Kumar Das,‡^a Etsuko Tokunaga,^a Kyosuke Harada,^a Yuji Sumii

^a and Norio Shibata

*^a

Author affiliations

* Corresponding authors

^a Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan
E-mail: nozshiba@nitech.ac.jp

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.

Download options Please wait...

Supplementary files

Supplementary information PDF (4007K)

Article information

DOI: https://doi.org/10.1039/C7QO00234C
Article type: Research Article
Submitted: 25 Mar 2017
Accepted: 22 May 2017
First published: 23 May 2017

Download Citation

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

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic Chemistry Frontiers

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

Abstract

Supplementary files

Article information

Download Citation

Permissions

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

Social activity

Search articles by author

Spotlight

Advertisements