Concise Synthesis of Broussonone A
Abstract
:1. Introduction
2. Results and Discussion
Entry | 8 (equiv.) | Catalyst (mol %) | Solvent | Yield (%) b |
---|---|---|---|---|
1 | 2.0 | Grubbs I (2) | THF | NR c |
2 | 2.0 | Grubbs II (2) | THF | 9 |
3 | 2.0 | Hoveyda-Grubbs II (2) | THF | 8 |
4 | 2.0 | Grubbs II (5) | THF | 41 |
5 | 2.0 | Grubbs II(10) | THF | 37 |
6 | 2.0 | Grubbs II (5) | CH2Cl2 | 4 |
7 | 2.0 | Grubbs II (5) | DCE | 12 |
8 | 2.0 | Grubbs II (5) | toluene | 11 |
9 | 1.0 | Grubbs II (5) | THF | 30 |
10 | 4.0 | Grubbs II (5) | THF | 36 |
11 | 2.0 | Grubbs II (5) | THF | 61 d |
Entry | Hypervalent Iodine | Solvent | Yield (%) b | |
---|---|---|---|---|
1 | 12 | |||
1 | PhI(OAc)2 | CH3CN/H2O (2/1) | 7 | 3 |
2 | PhI(OAc)2 | Acetone | 16 | 27 |
3 | PhI(OCOCF3)2 | CH3CN/H2O (2/1) | 38 | 31 |
4 | PhI(OCOCF3)2 | CH3CN | - | >49 |
5 | PhI(OCOCF3)2 | THF | - | >49 |
6 | PhI(OCOCF3)2 | Acetone | 40 | 31 |
7 | PhI(OCOCF3)2 | Acetone/H2O (2/1) | 22 | 21 |
8 | PhI(OCOCF3)2 | CH3OH/H2O (2/1) | - | 31 |
3. Experimental Section
3.1. General Information
3.2. Synthesis
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References and Notes
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Jo, H.; Choi, M.; Viji, M.; Lee, Y.H.; Kwak, Y.-S.; Lee, K.; Choi, N.S.; Lee, Y.-J.; Lee, H.; Hong, J.T.; et al. Concise Synthesis of Broussonone A. Molecules 2015, 20, 15966-15975. https://doi.org/10.3390/molecules200915966
Jo H, Choi M, Viji M, Lee YH, Kwak Y-S, Lee K, Choi NS, Lee Y-J, Lee H, Hong JT, et al. Concise Synthesis of Broussonone A. Molecules. 2015; 20(9):15966-15975. https://doi.org/10.3390/molecules200915966
Chicago/Turabian StyleJo, Hyeju, Minho Choi, Mayavan Viji, Young Hee Lee, Young-Shin Kwak, Kiho Lee, Nam Song Choi, Yeon-Ju Lee, Heesoon Lee, Jin Tae Hong, and et al. 2015. "Concise Synthesis of Broussonone A" Molecules 20, no. 9: 15966-15975. https://doi.org/10.3390/molecules200915966