| Budget Amount *help |
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2015: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2013: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
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| Outline of Final Research Achievements |
Two novel methods have been developed for the stereocontrolled synthesis of functionalized biaryl derivatives possessing both axial chirality and central chirality: (1) One utilizes enantioselective desymmetrization of achiral biphenyl-2,6-diyl diacetate derivatives through the lipase-catalyzed mono-hydrolysis for the control of axial stereochemistry. The subsequent diastereoselective construction of a stereogenic center on the side chain portion and the formation of the eight-membered carbocyclic bridge by ring-closing metathesis offers an efficient entry to the optically active dibenzocyclooctadiene core of gomicin/schsandrine-type lignans. The other method utilizes diastereoselective desymmetrization through the medium-sized lactone formation of a biphenyl-2,6-diol, which possesses, at the C2' position, an alkanoic-acid side chain containing a stereogenic center, enabling highly stereoselective access to a series of 8-10-membered lactone-annulated biphenyls.
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