Development of progressive asymmetric syntheses of alkaloid based on construction of heteroatom bridged compounds
| Project/Area Number |
24550116
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Shinshu University |
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Principal Investigator |
SUGA Hiroyuki 信州大学, 学術研究院工学系, 教授 (60211299)
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| Project Period (FY) |
2012-04-01 – 2015-03-31
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| Project Status |
Completed (Fiscal Year 2014)
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| Budget Amount *help |
¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2014: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2013: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2012: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
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| Keywords | 付加環化 / ジアゾ化合物 / キラルルイス酸 / エナンチオ選択性 / 生理活性 / カルボニルイリド / アゾメチンイリド |
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| Outline of Final Research Achievements |
Highly enantioselective 1,3-dipolar cycloaddition reactions between several 3-(2-alkenoyl)-2-oxazolidinones and cyclic carbonyl ylides that were generated from N-diazoacetyl lactams have been developed. Reactions of N-diazoacetyl lactams that possess 5-, 6-, and 7-membered rings were transformed to the corresponding epoxy-bridged indolizidines, quinolizidines, and 1-azabicyclo[5.4.0]undecanes with good to high enantioselectivities. The epoxy-bridged indolizidines were revealed to be important intermediates for the synthesis of optically active hydroxylated indolidizine derivatives. The cycloaddition reactions between N-methylindoles and 6-membered cyclic carbonyl ylides derived from 1-diazo-5-aryl-2,5-pentanedione precursors also showed high enantioselectivities along with relatively good exo-selectivities. Similar asymmetric cycloadditions of cyclic azomethine ylides derived from diazo imine derivatves have been developed to afford excellent to good enantioselectivities.
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Report
(4 results)
Research Products
(20 results)
