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Bicycloannulation: A one-step synthesis of tricyclo [3.2.1.02,7] octan-6-ones.

✍ Scribed by Robert M. Cory; Dominic M.T. Chan

Publisher: Elsevier Science
Year: 1975
Tongue: French
Weight: 171 KB
Volume: 16
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)91087-6

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✦ Synopsis

In recent years, a number of publlcatlons have appeared in which the tncyclo [3.2.1.02s7] octan-6-one system (1) IS utlllzed in synthetic intermediates as a convement precursor of blcycle [3 2.11 octane and blcyclo [2.2.2] octane systems.' All of these lnvestlgatlons have employed the copper-catalyzed intramolecular cycllzatlon of cyclohexenyl dlazomethyl ketones in the formatlon of the required tncycllc compounds_. Our Interest ln this structure (l_) derives from our planned syntheses of lshwarane and trachylobane terpenolds,*~' exempllfled by the parent hydrocarbons ,2 and ,3 respectively

We expected that lf the a'-enolate (_4) of an a,&cy-

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