A unique configuration-dependent mechanistic switch, observed when epimeric seco-acids are subjected to typical Mitsunobu lactonization conditions, is just one of the many unexpected, yet insightful surprises of a synthetic adventure culminating in the first enantioselective total synthesis of the novel microtubule-stabilizing natural product peloruside A (1).
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Liao et al. (2003) studied this question.
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