Intramolecular cyclopropanation-ring fragmentation leading to spirocyclic ring construction: a stereoselective synthesis of .beta.-chamigrene

Autor:	Denice M. Spero, Julian Adams, Carole Lepine-Frenette
Rok vydání:	1991
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Ketone Rhodium(II) acetate chemistry Intramolecular reaction Dihydropyran Cyclopropanation Stereochemistry Organic Chemistry Total synthesis Carbene Cyclopropane
Zdroj:	The Journal of Organic Chemistry. 56:4494-4498
ISSN:	1520-6904 0022-3263
Popis:	The transannular cyclopropanation of a keto carbene generated by Rh 2 (OAc) 4 catalysis on a bicyclic dihydropyran nucleus provided a key oxatricyclic ketone intermediate for the synthesis of the [6.6] spirocyclic ring construction. Selective fragmentation of the cyclopropane followed by hydrolytic cleavage of the C−O bond provided the spirocyclic skeleton. Functional group manipulations to adjust oxidation states led to a total synthesis of (±)-β-chamigrene in 14 steps without the use of protection/deprotection schemes
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b2b4cf223e0fc893d032af7b470118c7 https://doi.org/10.1021/jo00014a032 Zobrazit plný text záznamu