Synthesis of Juglone and its Derivatives

Jin Lan Wang; Zhong Jin Yang; Jian Jun Wang; Wan Xia Tang; Ming Zhao; Shu Jun Zhang

doi:10.4028/www.scientific.net/AMM.138-139.1139

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HomeApplied Mechanics and MaterialsApplied Mechanics and Materials Vols. 138-139Synthesis of Juglone and its Derivatives

Synthesis of Juglone and its Derivatives

Abstract:

Juglone (1), plumbagin (2) and isoplumbagin (3) were synthesized from the natural product 4,8-dihydroxy naphthol-β-D-glucoside (4) which existed large amount in barks of Juglans mandshurica. Juglone was achieved directly by deglycosylation catalyzing with CAS in 78 % yield. Plumbagin was synthesized by five steps with an overall yield of 22 %. Isoplumbagin was synthesized by six steps in 24 % yield.

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Applied Mechanics and Materials (Volumes 138-139)

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1139-1141

DOI:

https://doi.org/10.4028/www.scientific.net/AMM.138-139.1139

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Online since:

November 2011

Authors:

Jin Lan Wang, Zhong Jin Yang, Jian Jun Wang, Wan Xia Tang, Ming Zhao, Shu Jun Zhang

Keywords:

4,8-dihydroxynaphthol-β-D-glucoside, Isoplumbagin, Plumbagin

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References

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[7] Juglone (5-hydroxy-1, 4-naphthoquinone) (1): Mp 154 - 155 oC; MS (EI) m/z: 174; 1H NMR (400 MHz, CDCl3) δ: 11. 91 (1H, s, 5-OH) 7. 66 (1H, dd, J = 7. 6, 7. 6 Hz, H-7), 7. 63 (1H, dd, J = 7. 6, 2. 0 Hz, H-8), 7. 30 (1H, dd, J = 7. 6, 2. 0 Hz, H-6) 6. 96 (2H, s, H-2, 3).

DOI: 10.7554/elife.15104.015

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[8] Plumbagin (5-hydroxy-2-methyl-1, 4-naphthoquinone) (2): Mp 74 - 75 oC; MS (EI) m/z: 188; 1H NMR (400 MHz, CDCl3) δ: 11. 96 (1H, s, 5-OH), 7. 64 (1H, dd, J = 7. 5, 1. 4 Hz, H-8), 7. 60 (1H, dd, J = 7. 9, 7. 5 Hz, H-7), 7. 25 (1H, dd, J =7. 9, 1. 4 Hz, H-6), 6. 80 (1H, q, J = 1. 5 Hz, H-3), 2. 19 (3H, d, J = 1. 5 Hz, H-11). 13C NMR (100 MHz, CDCl3) δ: 190. 2 (C-4), 184. 7 (C-1), 161. 2 (C-5), 149. 6 (C-2), 136. 0 (C-7), 135. 4 (C-3), 132. 1 (C-9), 124. 1 (C-6), 119. 2 (C-8), 115. 1 (C-10), 16. 4 (C-11).

DOI: 10.7554/elife.15104.015

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[9] Isoplumbagin (5-hydroxy-3-methyl-1, 4-naphthoquinone) (3): Mp 158 - 159 oC; MS (EI) m/z: 188; 1H NMR (400 MHz, CDCl3) δ: 12. 07 (1H, s, 5-OH), 7. 60 (2H, m, H-7, 8), 7. 25 (1H, m, H-6), 6. 82 (1H, q, J = 1. 2 Hz, H-2), 2. 19 (3H, d, J = 1. 2 Hz, H-11). 13C NMR (100 MHz, CDCl3) δ: 190. 8 (C-4), 184. 2 (C-1), 161. 5 (C-5), 148. 0 (C-3), 136. 6 (C-7), 136. 4 (C-2), 132. 3 (C-9), 124. 1 (C-6), 118. 7 (C-8), 115. 1 (C-10), 16. 0 (C-11).

DOI: 10.7554/elife.15104.015

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