A Practical, Multi-gram Synthesis of (±)-Herbindole A, (±)-Herbindole B, and (±)-Herbindole C from a Common Intermediate via 6,7-Indole Aryne Cycloaddition and Pd(0)-Catalyzed Cross-Coupling Reactions

Autor:	Keith R. Buszek, Nalin Chandrasoma, Sivadarshini Pathmanathan
Rok vydání:	2015
Předmět:	Indole test Cyclopentadiene Negishi coupling Stereochemistry Organic Chemistry Regioselectivity Biochemistry Combinatorial chemistry Aryne Cycloaddition Coupling reaction Article Stille reaction chemistry.chemical_compound chemistry Drug Discovery
Zdroj:	Tetrahedron letters. 56(23)
ISSN:	0040-4039
Popis:	A practical, multi-gram 10-step synthesis of racemic herbindole A, B, and C from a common intermediate is described. The key step features a remarkably regioselective C-7 metal-halogen exchange and elimination from a Bartoli-generated N-t-butyldimethylsilyl-4,6,7-tribromo-5-methylindole scaffold to afford the 6,7-indole aryne. Cycloaddition with cyclopentadiene, oxidative cleavage, and Fujimoto reduction gave a common intermediate from which all three herbindoles were readily derived. A final Pd(0)-catalyzed Negishi and Stille cross-coupling reaction at the C-4 bromide afforded each of the herbindoles on a multigram scale.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::027dc054b6a86cfb32f6bdcc34a33f41 https://pubmed.ncbi.nlm.nih.gov/26516291 Zobrazit plný text záznamu Full Text from ScienceDirect