Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 2, Pages 920-923Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja211444m
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Funding
- State Key Laboratory of Bioorganic and Natural Products
- Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
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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 Diets-Alder reaction, a Pd-catalyzed O -> C allylic rearrangement, a chemoselective Wacker oxidation, and a Dieckmann condensation/hemiketalization cascade.
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