engleski

Total synthesis of Penicyclone A using a double Grignard reaction

We describe the first total synthesis of penicyclone A, a novel deep-sea fungus-derived polyketide, and a reevaluation of its antimicrobial activity. The synthesis of this unique spirolactone was achieved in ten steps starting from a known D-ribose derivative. The key steps include a double Grignard reaction for the diastereoselective construction of the chiral tertiary alcohol intermediate, tandem oxidation/cyclization, and a photooxygenation, followed by an oxidative rearrangement to introduce the enone functionality.

Total synthesis ; Penicyclone A ; Grignard reaction

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