Rearrangement of acyclic-alkyl [3.2.1]bicyclic alcohols to free methylene dimethyl alkyl [2.2.2]bicyclic octanes: application to preparation of stereospecific novel sesquiterpene and terpenoids

Autor:	Wei-Fan Lin, Chi-Yi Chang, Te-Fang Yang
Rok vydání:	2015
Předmět:	chemistry.chemical_classification Ketone Nucleophilic addition Bicyclic molecule Aryl Organic Chemistry Sesquiterpene Biochemistry chemistry.chemical_compound Stereospecificity chemistry Drug Discovery Organic chemistry Methylene Alkyl
Zdroj:	Tetrahedron Letters. 56:801-804
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2014.12.092
Popis:	Reaction of camphor-derived [3.2.1]bicyclic hydroxyl ketone with organolithium or Grignard reagents provided various alkyl/aryl [3.2.1]bicyclic diols, in which the secondary hydroxyl group was then protected and various acetoxy [3.2.1]bicyclic alcohols were obtained. Treatment of these acetoxy [3.2.1]bicyclic alcohols with TsOH in methanol at reflux afforded various methylene dimethyl alkyl/aryl [2.2.2]bicyclic octanes. For the application of the title reaction, some of these octanes were converted to stereospecific novel sesquiterpene and terpenoids.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b78efbbd34c311db83bae2ae437a8bb0 https://doi.org/10.1016/j.tetlet.2014.12.092 Zobrazit plný text záznamu Full Text from ScienceDirect