Preparation of 2,3-dihydroxycyclopentanone

The title compound seems easy to make, but actually costs a lot of steps, especially in enantiomeric form.

In the following paper, the auther had a new preparaion method.

Syntheses of (-)-Oleocanthal
by AB Smith III
J. Org. Chem. 2007, 72, 6891-6900

We began by adopting a protocol developed by Borchardt14 et al. (Scheme 6). Exhaustive
oxidation of 16 employing pyridinium chlorochromate (PCC) (4 equiv) provided lactone 17 in 62% yield. This transformation involves both oxidation of the primary alcohol and cleavage of
a C-C bond. Treatment of the resultant lactone (17) with the lithium anion derived from dimethyl methylphosphate produced enone (-)-18, which upon hydrogenolysis furnished ketone (-)- 11. The overall yield of (-)-11 from D-lyxose was reproducibly 50% on a 10 gram scale. Although D-lyxose is more expensive (ca. 3 times) than D-ribose, the starting material utilized in the first-generation synthesis, this sequence eliminates three steps, reduces the use of several expensive reagents, and is scalable. Equally important, only a single chromatographic separation is required after hydrogenolysis. Alkylation as achieved in the firstgeneration synthesis then afforded (-)-12 in 55-60% yield.





















Is the new way really good?
I don't know. But at least there is a big drawback they didn't say it here.
In the experimental, they described the pcc reaction which needs a lot of benzene (cause cancer) as solvent.