Budget Amount *help |
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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Outline of Final Research Achievements |
In this study we accomplished a total synthesis of MPC1001B, antiproliferative activity against DU145 human prostate cancer cell line, based on inversion of the two stereogenic centers that were generated in the key TBAF-mediated formation of the macrolactone. Preliminary experiments on introduction of the hydroxyl group on the dihydrooxepine skeleton for the late-stage oxidation were performed using a model substrate with selenium dioxide to establish mild oxidation conditions. We also investigated construction of the partial skeleton of aconitine through formation of enone from in five steps including Birch reduction. Conversion to the corresponding silyl enol ether followed by Diels-Alder reaction provided the desired tetracyclic compound, which was converted to the secondary alcohol. The mesylate was treated with silica gel to provide the allylic alcohol as a single isomer via Wagner-Meerwein rearrangement. Synthetic studies on acochlearine was also performed.
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