Issue 9, 2018

Nine-step total synthesis of (−)-strychnofoline

Abstract

Strychnofoline is a Strychnos alkaloid that has unique spirooxindole architecture and possesses important anticancer activity. Here, we have, for the first time, reported the enantioselective synthesis of strychnofoline proceeding in only nine steps from commercially available 6-methoxytryptamine. The efficiency of the synthesis derives from the use of two sequential transformation steps in the catalytic asymmetric construction of the spiro[pyrrolidine-3,3′-oxindole] motif in a facile manner. Our route is amenable to the synthesis of other natural and synthetic analogs of bioactive spirooxindole alkaloids to access their therapeutic potential.

Graphical abstract: Nine-step total synthesis of (−)-strychnofoline

Supplementary files

Article information

Article type
Communication
Submitted
21 Nov. 2017
Accepted
06 Janv. 2018
First published
08 Janv. 2018

Chem. Commun., 2018,54, 1125-1128

Nine-step total synthesis of (−)-strychnofoline

Q. Yu, P. Guo, J. Jian, Y. Chen and J. Xu, Chem. Commun., 2018, 54, 1125 DOI: 10.1039/C7CC08938D

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