Concise Total Syntheses of Dipiperidine Alkaloids Virgidivarine and Virgiboidine through Ru-Mediated Ene-Ene-Yne Ring Rearrangement Metathesis (RRM)

Autor:	Steffen Kress, Jochen Weckesser, Sabrina R. Schulz, Siegfried Blechert
Rok vydání:	2013
Předmět:	chemistry.chemical_compound Dihydroxylation Stereochemistry Chemistry Organic Chemistry Enantioselective synthesis Total synthesis Stereoselectivity Physical and Theoretical Chemistry Glycol cleavage Metathesis Ene reaction Organometallic chemistry
Zdroj:	European Journal of Organic Chemistry. 2013:1346-1355
ISSN:	1434-193X
DOI:	10.1002/ejoc.201201516
Popis:	Herein, we report on the first enantioselective synthesis of the sparteine-type alkaloids virgidivarine (1) and virgiboidine (2). The stereoselective construction of the challenging dipiperidine core within 1 and 2 was realized by applying an intramolecular ene-ene-yne ring-rearrangement metathesis (RRM) protocol. In combination with this sequence, an unprecedented tandem metathesis/oxidation reaction was established. Subsequent to the RRM event, the Ru-alkylidene species was converted into the highly potent dihydroxylation catalyst RuO4 by the addition of NaIO4. This transformation rendered five sequential reactions that include an ene-ene-yne RRM/dihydroxylation/glycol cleavage in a one-pot procedure. This approach provides practical and general access to dipiperidines and piperidino-quinolizidines. Despite their wide use in organic and organometallic chemistry as well as their occurrence in biologically active natural products, methods are still lacking for the stereoselective synthesis of these motifs.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::d317bae33a6fa556ca395ea5f5da650f https://doi.org/10.1002/ejoc.201201516 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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