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2019 年度 実績報告書

Synthetic Strategies for the Total Synthesis of Pyranonaphthoquinone Type Natural Products

研究課題

研究課題/領域番号 19K21125
配分区分基金
研究機関東京工業大学

研究代表者

マツリ マーク・マルセロ  東京工業大学, 理学院, 特任助教 (60829315)

研究期間 (年度) 2019-04-01 – 2020-03-31
キーワードtotal synthesis / pyranonapthoquinons / Claisen rearrangement / aromatic polyketides
研究実績の概要

The efficient and large-scale synthesis of two building blocks has been achieved. For the Synthesis of the aromatic building block, a three-step protocoll has been developed and partly published. The methodology developed includes highly regioselective benzocyclobutenol formation followed by bond-selective ring cleavage and cyclobuten ring opening to access o-methylbenzaldehydes.
An efficient annulation protocol allowed assembly of a naphthalene precursor. The synthesis of a Claisen-precursor was optimized and allowed synthesis of the latter in 12 steps.
The dearomative Claisen rearrangement (CR) was first investigated with a deuterium-labelled model compound. The results strongly suggest a reaction pathway following the classical CR via a 3,3-sigmatropic shift.
Optimization of the reaction conditions for the CR on the real system was developed and comprises a two-step protocol.
The developed synthesis allows for the construction of a synthetic intermediate for ruthmycin bearing the full carbon skeleton with an angular stereogenic center with perfect stereocontrol.

  • 研究成果

    (2件)

すべて 2019

すべて 学会発表 (2件)

  • [学会発表] Synthetic Studies on b-Naphthocyclinone (2): Design, Preparation and Reactivity of a Donor Unit2019

    • 著者名/発表者名
      Mark M. Maturi
    • 学会等名
      CSJ 99th Symposium
  • [学会発表] Towards b-Naphthocyclinone Synthetic Studies and Strategies2019

    • 著者名/発表者名
      Mark M. Maturi
    • 学会等名
      Symposium on the Chemistry of Natural Products

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公開日: 2021-01-27  

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