An Efficient Synthesis of Carlosic Acid and Other 5-Carboxymethyltetronates from Malates

2005 
S-Carlosic acid was prepared in six steps and 32% yield from malic acid. Ring closure was effected by a domino addition-Wittig alkenation reaction with Ph 3 PCCO. A variant employing resin-bound malates furnished immobilized 5-carboxymethyltetronates. It should be amenable to parallelization and automation.
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