Racemic Marinopyrrole B by Total Synthesis

Overview

Journal Chem Commun (Camb)

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2012 Nov 7

PMID 23128288

Citations 6

Authors

Ping Cheng

Derrick L J Clive

Shimal Fernandopulle

Zhenhua Chen

Affiliations

Soon will be listed here.

Abstract

The first synthesis of marinopyrrole B, which is highly active against methicillin-resistant Staphylococcus aureus, is described. The route involved constructing a pyrrole ring on the nitrogen of a 3-bromo-4,5-dichloropyrrole by N-alkylation with a special Michael acceptor having an allylic leaving group; the second pyrrole ring was then formed by a Paal-Knorr reaction.

Citing Articles

200 Years of The Haloform Reaction: Methods and Applications.

Rowett A, Heard D, Koria P, Dean A, Sweeting S, Lennox A Chemistry. 2024; 30(71):e202403045.

PMID: 39345024 PMC: 11653256. DOI: 10.1002/chem.202403045.

Marine Pyrrole Alkaloids.

Seipp K, Geske L, Opatz T Mar Drugs. 2021; 19(9).

PMID: 34564176 PMC: 8471394. DOI: 10.3390/md19090514.

Marinopyrrole derivatives with sulfide spacers as selective disruptors of Mcl-1 binding to pro-apoptotic protein Bim.

Cheng C, Liu Y, Balasis M, Garner T, Li J, Simmons N Mar Drugs. 2014; 12(8):4311-25.

PMID: 25076060 PMC: 4145318. DOI: 10.3390/md12084311.

Marinopyrrole derivatives as potential antibiotic agents against methicillin-resistant Staphylococcus aureus (III).

Liu Y, Haste N, Thienphrapa W, Li J, Nizet V, Hensler M Mar Drugs. 2014; 12(5):2458-70.

PMID: 24796304 PMC: 4052300. DOI: 10.3390/md12052458.

Cyclic marinopyrrole derivatives as disruptors of Mcl-1 and Bcl-x(L) binding to Bim.

Cheng C, Liu Y, Balasis M, Simmons N, Li J, Song H Mar Drugs. 2014; 12(3):1335-48.

PMID: 24608970 PMC: 3967213. DOI: 10.3390/md12031335.