Total synthesis of chloptosin: a dimeric cyclohexapeptide

Autor:	Alexander J. Oelke, Francesca Antonietti, Leonardo Bertone, Philippa B. Cranwell, David J. France, Rebecca J. M. Goss, Tatjana Hofmann, Stephan Knauer, Steven J. Moss, Paul C. Skelton, Richard M. Turner, Georg Wuitschik, Steven V. Ley
Rok vydání:	2010
Předmět:	Steric effects Tandem Molecular Structure Stereochemistry Organic Chemistry Total synthesis Stereoisomerism General Chemistry Combinatorial chemistry Peptides Cyclic Catalysis Stille reaction Pyridazines chemistry.chemical_compound chemistry Organocatalysis Chloptosin Tetrazole
Zdroj:	Chemistry (Weinheim an der Bergstrasse, Germany). 17(15)
ISSN:	1521-3765
Popis:	Here we describe in full our investigations into the synthesis of the dimeric cyclohexapeptide chloptosin in 17 linear steps. Particularly, this work features an organocatalytic tandem process for the synthesis of the embedded piperazic acids, in which a differentially protected azodicarboxylate is used together with pyrrolidinyl tetrazole as the catalyst. The central biaryl bond is being formed by Stille coupling of two sterically demanding ortho-chloropyrroloindole fragments. The inherent flexibility of the synthetic strategy proved beneficial as the route could be adjusted smoothly during the progression of the synthesis programme.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0f26c703fc1ff030b98deb4ebb8b446a https://pubmed.ncbi.nlm.nih.gov/21412862 Zobrazit plný text záznamu Plný text