Total Synthesis of (−)-Fusarisetin A and Reassignment of the Absolute Configuration of Its Natural Counterpart
Journal of the American Chemical Society2011Vol. 134(2), pp. 920–923
Citations Over TimeTop 10% of 2011 papers
Abstract
The first total synthesis of (-)-fusarisetin A, the enantiomer of naturally occurring acinar morphogenesis inhibitor (+)-fusarisetin A, was accomplished in 13 steps, leading to the reassignment of the absolute configuration of the natural product. The synthesis featured a Lewis acid-promoted intramolecular Diels-Alder reaction, a Pd-catalyzed O→C allylic rearrangement, a chemoselective Wacker oxidation, and a Dieckmann condensation/hemiketalization cascade.
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