Issue 68, 2016

Collective formal synthesis of (±)-rhynchophylline and homologues

Abstract

A collective formal synthesis approach to bioactive oxindole alkaloids, including (±)-rhynchophylline, (±)-isorhynchophylline, (±)-mitraphylline, (±)-formosanine, (±)-isomitraphylline, and (±)-isoformosanine, is completed in a protecting-group free manner. Besides multigram-scaled operations, the notable feature of the synthesis is the application of two one-pot, sequential transformations. Namely, two key tetracyclic intermediates pyridinium salt 9 and monoester 14 were prepared by a one-pot N-alkylation/cross-dehydrogenative coupling sequence and a one-pot Michael/Karpocho sequence with minimal purification, respectively.

Graphical abstract: Collective formal synthesis of (±)-rhynchophylline and homologues

Supplementary files

Article information

Article type
Paper
Submitted
17 พ.ค. 2559
Accepted
25 มิ.ย. 2559
First published
28 มิ.ย. 2559

RSC Adv., 2016,6, 63131-63135

Collective formal synthesis of (±)-rhynchophylline and homologues

J. Xu, L. Shao, X. Shi, J. Ren, C. Xia and Q. Zhao, RSC Adv., 2016, 6, 63131 DOI: 10.1039/C6RA12766E

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.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements