Total synthesis of natural products through synthetic strategy based on enovative catalysis
| Project/Area Number |
23390004
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Kyoto University |
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Principal Investigator |
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| Project Period (FY) |
2011-04-01 – 2014-03-31
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| Project Status |
Completed (Fiscal Year 2013)
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| Budget Amount *help |
¥18,850,000 (Direct Cost: ¥14,500,000、Indirect Cost: ¥4,350,000)
Fiscal Year 2013: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2012: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2011: ¥10,140,000 (Direct Cost: ¥7,800,000、Indirect Cost: ¥2,340,000)
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| Keywords | 複素環化学 / 全合成 / 不斉合成 / 環化反応 / アポトーシス / 多剤耐性抗結核作用 / perophoramidine / caprazamycin / アミジン / ハロゲンーリチウム交換反応 / 第四級炭素 / 1,4-ジアゼパノン / アンチβ―ヒドロキシ―α―アミノ酸 / 光延反応 / caprazamycin B / アルドール反応 / ジヒドロジアゼピノン / ヒドロアミド化反応 / 2置換アミノ酸 / ダブルシアノアミド化反応 / カルボジイミド / ヨウ化サマリウム / 4級スピロ炭素骨格 / Caprazamycin B / β-ヒドロキシカルボン酸 / グルタル酸モノエステル |
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| Research Abstract |
In this research project, we focused on the total synthesis of perophoramidine and caprazamycin B. Concerning perophoramidine, we have developed the SmI2-mediated cyclization of unsaturated lactams or amidines bearing a carbodiimide moiety as well as the dearomatizing conjugate addition to quinoline derivatives including a lactam or amidine, to construct a spirocyclic quaternary carbon center and a five-membered amidine ring. By using these original synthetic tools, total synthesis of dehaloperophoramidine was achieved. For the caprazamycin synthesis, we explored the organocatalyzed asymmetric syntheses of fatty acid side chains and hydroxyamino acids bearing a uridine. Furthermore, diazepanone rings were also synthesized by using an Au- or Pt-catalyzed hydroamidation or Mitsunobu reaction. As a result, we succeed in the introduction of the fatty acid side chain into a model compound bearing a diazepanone ring as well as the transformation into the protected caprazol derivative.
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Report
(4 results)
Research Products
(82 results)
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[Presentation] 中村斐有2013
Author(s)
Caprazamycin Aの合成研究
Organizer
日本薬学会第133年会
Place of Presentation
パシフィコ横浜（神奈川県）
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[Presentation] 石田貴之2012
Author(s)
Perophoramidineの全合成研究
Organizer
第10回次世代を担う有機化学シンポ ジウム
Place of Presentation
大阪大学銀杏会館（大阪府）
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