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2016 Fiscal Year Final Research Report

Development and Application of Convergent Strategies for Unified Total Syntheses of Architecturally Complex Natural Products

Research Project

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Project/Area Number 26253003
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionThe University of Tokyo

Principal Investigator

Inoue Masayuki  東京大学, 大学院薬学系研究科(薬学部), 教授 (70322998)

Co-Investigator(Renkei-kenkyūsha) URABE Daisuke  東京大学, 大学院薬学系研究科, 講師 (80503515)
NAGATOMO Masanori  東京大学, 大学院薬学系研究科, 助教 (70634161)
TAKEFUMI Kuranaga  東京大学, 大学院薬学系研究科, 助教 (70625201)
Project Period (FY) 2014-04-01 – 2017-03-31
Keywords合成化学 / 全合成 / 生物活性分子の設計 / 生理活性 / 収束的合成 / ラジカル反応
Outline of Final Research Achievements

Architecturally complex and densely oxygenated natural products often have potent and selective biological activities. In this study, we focused on efficient, practical and flexible syntheses of these natural products based on radical chemistry. We developed an a-alkoxy radical methodology for assembly of two- and three components, and efficient radical-radical homo- and heterocoupling reactions of a-alkoxy radicals. By taking advantage of these strategies, we realized the total syntheses of various complex natural products, including ryanodine, crotophorbolone, 4-hydroxyzinowol, oubagenin, and zaragozic acid C. Moreover, these synthetic routes were applied to unified preparation of the structurally related compounds for the future structure-activity relationship studies. Because of the broadness of the reaction scope and the mildness of the conditions, these powerful strategies introduce novel technologies for expedited total synthesis of densely oxygenated natural products.

Free Research Field

天然物合成化学・生物有機化学

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Published: 2018-03-22  

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