Catalytic Enantioselective Synthesis of a Pyrrolizidine-Alkaloid-Inspired Compound Collection with Antiplasmodial Activity

Zhi Jun Jia, Hiroshi Takayama, Yushi Futamura, Harumi Aono, Jonathan O. Bauer, Carsten Strohmann, Andrey P. Antonchick*, Hiroyuki Osada, Herbert Waldmann

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

A novel enantioselective approach to the synthesis of a compound collection inspired by natural pyrrolizidine alkaloids was developed, employing an enantioselectively catalyzed 1,3-dipolar cycloaddition as the key step. The cycloadducts were obtained with excellent enantio- and diastereoselectivity. Biological evaluation of the resulting compound collection revealed that the compound class has multiple bioactivities, including activity against Plasmodium falciparum 3D7 and inhibition of Hedgehog signaling.

Original languageEnglish
Pages (from-to)7033-7041
Number of pages9
JournalJournal of Organic Chemistry
Volume83
Issue number13
DOIs
Publication statusPublished - 2018 Jul 6
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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