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Synthesis 1991; 1991(11): 963-965
DOI: 10.1055/s-1991-26617
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A Practical Method for the Synthesis of Homochiral 2,10-Camphanediols

Deng Jingen* , Jiang Yaozhong, Liu Guilan, Wu Lanjun, Mi Aiqiao
  • *Chengdu Institute of Organic Chemistry, Academia Sinica, Chengdu 610015, People's Republic of China
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Publikationsdatum:
29. April 2002 (online)

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The esters 3a and 3b are conveniently prepared from (+)-ketopinic acid (7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-car-boxylate, 1) and are subsequently reduced to afford exo- and endo-2,10-camphanediols [1-(hydroxymethyl)-7,7-dimethylbicyclo [2.2.1]heptan-2-ols, 4a and 4b, respectively] in good overall yield. The alkylation of ester 3a with buyllithium gives only exo-10,10-dibutyl-2,10-camphanediol [exo-1-(1-butyl-1-hydroxypentyl)-7, 7-dimethylbicyclo[2.2.1]heptan-2-ol, 5] in good yield.