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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 13, Number 2
BKCSDE 13(2)
February 20, 1992

Title	Transformation of Bicyclic Ketal Compound to 1,2-Cyclopentanediol via 1,5-Diketone
Author	Jong-Gab Jun*, Dong Gyun Shin, Hyun Shun Shin, Sung Hoon Kim
Keywords
Abstract	New method for preparing cyclopentanediol from bicyclic ketal is described. Bicyclic ketal is cleaved to give 1,5-diketone, which is then reductively coupled intramolecularly to yield 1,2-cyclopentanediol. A solution of bicyclic ketal (1a) in methylene chloride was treated with aluminum chloride(2 eq.)-sodium iodide(l.5 eq.) at ambient temperature for 3 h to give the 1,5-diketone (2a) in 71% yield after basic work-up followed by short path column chromatography. A solution of the 1,5-diketone (2a) in THF was reacted with titanium tetrachloride(6 eq.)-Mg(Hg)(0.3 eq.) at 0℃ for 4 h to give the 1,2-cyclopentanediol (3a) in 75% yield after basic work-up followed by short path column chromatography.
Page	176 - 179
Full Text	PDF

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