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 Cax 2016
Accepted
25 Qas 2016
First published
28 Qas 2016

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

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