| Budget Amount *help |
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2016: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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| Outline of Final Research Achievements |
We found that a concerted catalyst system, Rh/C and chiral ruthenium complex, allowed the hydrogenation of salicylates to proceed with high stereoselectivities. Ethyl salicylate was transformed to 91% ee of ethyl trans-2-hydroxycyclohexanecarboxylate with trans/cis = 91/9. The resulting optically active cyclohexane was transformed into a compound bearing juvenile hormone activity, as follows: (1) The ester was transformed into its Weinreb amide. The Weinreb amide was treated with aryllithium to give the ketone. The ketone carbonyl was reduced to methylene through the hydrogenation with Pd/C catalyst and a Lewis acid. The alkylation of the products gave the target compound.
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