3 years ago

Formal Total Syntheses of (−)- and (+)-Actinophyllic Acid

Formal Total Syntheses
of (−)- and (+)-Actinophyllic
Dan Zhang, Yong Qin, Xiao-Yu Liu, Liping He, Fei Xue, Huifang Lu, Wenfei Li
The formal total syntheses of (−)-actinophyllic acid and its enantiomer starting from the same chiral intermediate are reported. The synthesis features a photoredox organocatalytic asymmetric alkylation to generate the original C15 chirality, a photocatalytic C–H functionalization of 3-methylindole in flow for constructing the C16 all-carbon quaternary center, a regioselective 1,3-dipolar cycloaddition, and an intramolecular Henry reaction to assemble the pentacyclic core of the target molecule.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02747

DOI: 10.1021/acs.joc.7b02747

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