Absolute Configuration and Enantioselective Synthesis of Spiculisporic Acid.

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Abstract
The absolute configuration of spiculisporic acid (1), obtained from Penicillium spiculisporum Lehman, was determined as (3S,4S) by a degradation into (2S,3S)-decylcitric acid (2), a metabolite of a variant of this fungus. The key step in the enantioselective synthesis of 1 from D-glucose was the nucleophilic addition to the ketone 6. Whereas the organolithium reagent 11 (a new homoenolate anion equivalent) led mainly to the desired equatorial addition, the corresponding Grignard reagent led to the opposite stereochemistry. There was evidence (GLC-MS) that P. spiculisporum also produces 3-hydroxy-1,3,4-dodecanetricarboxylic acid and 3-hydroxy-1,3,4-tridecanetricarboxylic acid.

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