Asymmetric synthesis of gonytolide A: strategic use of an aryl halide blocking group for oxidative coupling
Reichl, Kyle D.
Porco, John A.
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Citation (published version)Xiaowei Wu, Takayuki Iwata, Adam Scharf, Tian Qin, Kyle D Reichl, John A Porco. 2018. "Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling." JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Volume 140, Issue 18, pp. 5969 - 5975. https://doi.org/10.1021/jacs.8b02535
The first synthesis of the chromanone lactone dimer gonytolide A has been achieved employing vanadium(V)-mediated oxidative coupling of the monomer gonytolide C. An o-bromine blocking group strategy was employed to favor para- para coupling and to enable kinetic resolution of (±)-gonytolide C. Asymmetric conjugate reduction enabled practical kinetic resolution of a chiral, racemic precursor and the asymmetric synthesis of (+)-gonytolide A and its atropisomer.