Total Synthesis of ( ± )-α-Cubebene and ( ± )-β-Cubebene

Autor:	Edward Piers, Ronald W. Britton, William De Waal
Rok vydání:	1971
Předmět:	chemistry.chemical_compound Stereochemistry Chemistry Yield (chemistry) Organic Chemistry Intramolecular cyclization Total synthesis General Chemistry Sulfate Catalysis
Zdroj:	Canadian Journal of Chemistry. 49:12-19
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v71-003
Popis:	An efficient total synthesis of the racemic forms of the novel tricyclic sesquiterpenes α-cubebene (1) and β-cubebene (2) is described. The key step of this synthesis involved the cupric sulfate catalyzed intramolecular cyclization of the olefinic diazoketone 3, which produced, in high yield, ( ± )-β-cubebene norketone (24) and ( ± )-1,6-epi-β-cubebene norketone (25), in a ratio of approximately 3:5, respectively.
Databáze:	OpenAIRE
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