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The synthesis of dendroflorin
Yi Deng1,2, Kun Jiang1, Mao-Jun Cai3
1a Department of Natural Medicinal Chemistry , Shanghai Insitute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203 , China.
Journal of Asian Natural Products Research
|May 10, 2017
Summary
Researchers achieved the first synthesis of dendroflorin in 10 steps. A key Suzuki-Miyaura reaction formed the biphenyl structure, and an ortho-localization effect was observed during bromination.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Dendroflorin is a natural product with potential biological activities.
- Efficient synthetic routes are crucial for accessing complex molecules like dendroflorin.
Purpose of the Study:
- To report the first total synthesis of dendroflorin.
- To explore key reactions for constructing the dendroflorin scaffold.
Main Methods:
- Multi-step organic synthesis.
- Suzuki-Miyaura cross-coupling reaction for biphenyl formation.
- Electrophilic aromatic substitution (bromination) with analysis of regioselectivity.
Main Results:
- Successful 10-step synthesis of dendroflorin.
- Overall yield of 5.5% achieved.
- Observation and discussion of an ortho-localization effect during bromination of an intermediate.
Conclusions:
- The first total synthesis of dendroflorin was accomplished.
- The Suzuki-Miyaura reaction is effective for constructing the core biphenyl moiety.
- The study highlights regioselectivity in electrophilic aromatic substitution reactions.
