Total synthesis of (-)-fusarisetin A and reassignment of the absolute configuration of its natural counterpart |
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| Authors: | Deng Jun Zhu Bo Lu Zhaoyong Yu Haixin Li Ang |
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| Institution: | State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China. |
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| 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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