2018 Fiscal Year Annual Research Report
Synthetic Strategies for the Total Synthesis of Pyranonaphthoquinone Type Natural Products
| Project/Area Number |
18H05972
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| Allocation Type | Single-year Grants |
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| Research Institution | Tokyo Institute of Technology |
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Principal Investigator |
マツリ マーク・マルセロ 東京工業大学, 理学院, 特任助教 (60829315)
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| Project Period (FY) |
2018-08-24 – 2020-03-31
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| Keywords | natural products / total synthesis |
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| Outline of Annual Research Achievements |
The highly efficient synthesis of two crucial building blocks has been achieved. The aromatic building block was synthesized in three steps from a commercially available bromoarene, featuring aryne 2+2 cycloaddition, ring-opening and oxidative esterification. Furthermore, the synthesis of the dihydropyrone building block was optimized and a reliable route was established. This allowed for the large-scale synthesis of this building block in optically pure form (synthesis was performed for the enantiomer) in five steps from a commercially available and optically pure compound (both enantiomers commercially available). Additionally, chiral HPLC analysis of viable intermediates (racemic) was established to access the optical purity in the synthesis of enantiopure material.
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| Current Status of Research Progress |
Current Status of Research Progress
3: Progress in research has been slightly delayed.
Reason
Current progress of this research is not as far as expected. Reasons for the fallback behind schedule are due to personnel. Health related issues (of psychological nature) of a student co-worker made it impossible for said co-worker to continue the research on this project. For the safety and well-being, it was decided suspend said co-workers collaboration and work on the project.
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| Strategy for Future Research Activity |
The synthesis of a dihydropyrone annulated naphthalene - a key intermediate to various members of the pyranonaphthoquinone family - as well as its the efficient modification and the investigation of a dearomative Claisen rearrangement will be conducted.
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