Synthetic studies on nemorosone via enantioselective intramolecular cyclopropanation

Autor:	Aya Saito, Masahisa Nakada, Masahito Abe
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Ketone Bicyclic molecule Cyclopropanation Stereochemistry Organic Chemistry Enantioselective synthesis Total synthesis Alkylation Biochemistry Stereocenter chemistry Intramolecular force Drug Discovery
Zdroj:	Tetrahedron Letters. 51:1298-1302
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2009.12.147
Popis:	This Letter describes synthetic studies of nemorosone via enantioselective intramolecular cyclopropanation. For the total synthesis of nemorosone, three potential intermediates were evaluated through the efficiency of three sequential reactions, namely, their intramolecular cyclopropanation, dimethylation of the resultant cyclopropanes, and ring-opening reaction of the alkylated cyclopropanes. As a result, α-diazomethyl ketone 10c was found to be the most suitable. The enantioselective intramolecular cyclopropanation to construct the bicyclo[3.3.1]nonane core and preparation of the compound with all the correct stereogenic centers of nemorosone are also described.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::dd6fb2e303b5c30e20ecab6c8ff8150e https://doi.org/10.1016/j.tetlet.2009.12.147 Zobrazit plný text záznamu Full Text from ScienceDirect