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Modular Total Syntheses of the Alkaloids Discoipyrroles A and B, Potent Inhibitors of the DDR2 Signaling Pathway

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Date

2016-02-19

Authors

Zhang, Yiwen
Banwell, Martin
Carr, Paul D
Willis, Anthony

Journal Title

Journal ISSN

Volume Title

Publisher

American Chemical Society

Abstract

The title natural product 1 has been synthesized by treating the 1,2,3,5-tetrasubstituted pyrrole 23 with oxoperoxymolybdenum(pyridine) (hexamethylphosphoric triamide) (MoOPH). Compound 23 was itself prepared in seven steps from parent pyrrole using Ullmann-Goldberg and Suzuki-Miyaura cross-coupling, Vilsmeier-Haack formylation, electrophilic bromination, and Wittig olefination reactions as key steps. Related chemistry has been used to prepare discoipyrrole B (2).

Description

Keywords

alkaloids, biological products, discoidin domain receptors, heterocyclic compounds, 3-ring, molecular structure, pyrroles, pyrrolidinones, receptor protein-tyrosine kinases, receptors, mitogen, signal transduction, stereoisomerism

Citation

URI

http://hdl.handle.net/1885/219211

Collections

ANU Research Publications

Source

Organic letters

Type

Journal article

Book Title

Entity type

Access Statement

Open Access

License Rights

DOI

10.1021/acs.orglett.5b03672

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