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Lindbladione ( 1 ) is a neural stem cell differentiation activator isolated from  Lindbladia tubulina  by our group. Hes1 dimerization inhibitory activity of lindbladione ( 1 ) was discovered using our original fluorescent Hes1 dimer microplate assay. We also found that lindbladione ( 1 ) accelerates the differentiation of neural stem cells. We conducted the first total synthesis of lindbladione ( 1 ) via Heck reaction of 1-hexene-3-one  7  with iodinated naphthoquinone  12 , which was provided by Friedel–Crafts acylation followed by Claisen condensation, in the presence of Pd (II) acetate. Careful deprotection of the benzyl groups of  13  successively provided lindbladione ( 1 ). Synthesized lindbladione ( 1 ) exhibited potent Hes1 dimer inhibition (IC 50  of 2.7 μM) in our previously developed fluorescent Hes1 dimer microplate assay. Synthesized lindbladione ( 1 ) also accelerated the differentiation of C17.2 mouse neural stem cells into neurons dose dependently, increasing the number of neurons by 59% (2.5 μM) and 112% (10 μM) compared to the control. These activities are comparable to those of naturally occurring lindbladione ( 1 ) isolated from  L. tublina .

Total synthesis of lindbladione, a Hes1 dimerization inhibitor and neural stem cell activator isolated from Lindbladia tubulina