Annelation of 2,3-dimethylcyclohexanone. Synthetic proof for the stereochemistry of the sesquiterpene aristolone

Autor:	Edward Piers, William De Waal, Ronald W. Britton
Rok vydání:	1969
Předmět:	chemistry.chemical_classification Annulation Stereochemistry Organic Chemistry General Chemistry Sesquiterpene Levorotatory Enol Catalysis chemistry.chemical_compound chemistry Organic chemistry Stereoselectivity Methyllithium Aristolone Lactone
Zdroj:	Canadian Journal of Chemistry. 47:4307-4312
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v69-714
Popis:	An efficient annelation of 2,3-dimethylcyclohexanone is described. The key step of this process involves the reaction of the enol lactone 16 with methyllithium, under carefully controlled conditions. The completely stereoselective conversion of the sesquiterpene (−)-aristolone (1) into the levorotatory decalone 22b is described. Comparison of the latter with the unambiguously synthesized racemic decalone 22a conclusively establishes the relative stereochemistry of aristolone (1).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b811c7579f902b092115cb7ac8fa6598 https://doi.org/10.1139/v69-714 Zobrazit plný text záznamu