SCOPUS 정보 검색 플랫폼

Volumn 5, Issue 3, 2008, Pages 234-236

Concise formal synthesis of (±)-shikonin via a highly α-regioselective prenylation of 1, 4, 5, 8-tetramethoxynaphthalene-2-carbaldehyde

Author keywords

Oxonia cope rearrangement; Prenylation; Regioselectivity; Shikonin; Synthesis

Indexed keywords

EID: 50149084698 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/157017808783955899 Document Type: Article

Times cited : (9)

References (28)

1
- 0026458552
- Fujii, N.; Yamashita, Y.; Arima, Y.; Nagashima, M.; Nakano, H. Antimicrob. Agents Chemother., 1992, 36, 2589.
- (1992) Antimicrob. Agents Chemother , vol.36 , pp. 2589
- Fujii, N.¹ Yamashita, Y.² Arima, Y.³ Nagashima, M.⁴ Nakano, H.⁵

2
- 0028188983
- Wang, W. J.; Bai, J. Y.; Lui, D. P.; Xue, L. M.; Zhu, X. Y. Yaoxue Xuebao, 1994, 29, 161.
- (1994) Yaoxue Xuebao , vol.29 , pp. 161
- Wang, W.J.¹ Bai, J.Y.² Lui, D.P.³ Xue, L.M.⁴ Zhu, X.Y.⁵

3
- 0036581930
- Sasaki, K; Abe, H; Yoshizaki, F. Biol. Pharm. Bull., 2002, 25, 669.
- (2002) Biol. Pharm. Bull , vol.25 , pp. 669
- Sasaki, K.¹ Abe, H.² Yoshizaki, F.³

4
- 0037140829
- Lu, Q.; Liu, W.; Ding, J.; Cai, J.; Duan, W. Bioorg. Med. Chem. Lett., 2002, 12, 1375.
- (2002) Bioorg. Med. Chem. Lett , vol.12 , pp. 1375
- Lu, Q.¹ Liu, W.² Ding, J.³ Cai, J.⁴ Duan, W.⁵

5
- 0026720637
- Seto, Y.; Motoyoshi, S.; Nakamura, H.; Imuta, J.; Ishitoku, T.; Isayama, S. Yakugaku Zasshi, 1992, 112, 259.
- (1992) Yakugaku Zasshi , vol.112 , pp. 259
- Seto, Y.¹ Motoyoshi, S.² Nakamura, H.³ Imuta, J.⁴ Ishitoku, T.⁵ Isayama, S.⁶

6
- 0028916381
- Ahn, B. Z.; Baik, K. U.; Kweon, G. R.; Lim, K.; Hwang, B. D. J. Med. Chem., 1995, 38, 1044.
- (1995) J. Med. Chem , vol.38 , pp. 1044
- Ahn, B.Z.¹ Baik, K.U.² Kweon, G.R.³ Lim, K.⁴ Hwang, B.D.⁵

7
- 0008742582
- Plyta, Z. F.; Li, T.; Papageorgiou, V. P.; Mellidis, A. S.; Assimopoulou, A. N.; Pitsinos, E. N.; Couladouros, E. A. Bioorg. Med. Chem. Lett., 1998, 8, 3385.
- (1998) Bioorg. Med. Chem. Lett , vol.8 , pp. 3385
- Plyta, Z.F.¹ Li, T.² Papageorgiou, V.P.³ Mellidis, A.S.⁴ Assimopoulou, A.N.⁵ Pitsinos, E.N.⁶ Couladouros, E.A.⁷

8
- 0033575723
- Song, G. Y.; Zheng, X. G.; Kim, Y.; You, Y. J.; Sok, D. E.; Ahn, B. Z. Bioorg. Med. Chem. Lett., 1999, 9, 2407.
- (1999) Bioorg. Med. Chem. Lett , vol.9 , pp. 2407
- Song, G.Y.¹ Zheng, X.G.² Kim, Y.³ You, Y.J.⁴ Sok, D.E.⁵ Ahn, B.Z.⁶

9
- 0034113785
- Song, G. Y.; Kim, Y.; Zheng, X. G.; You, Y. J.; Cho, H.; Chung, J. H.; Sok, D. E.; Ahn, B. Z. Eur. J. Med. Chem., 2000, 35, 291.
- (2000) Eur. J. Med. Chem , vol.35 , pp. 291
- Song, G.Y.¹ Kim, Y.² Zheng, X.G.³ You, Y.J.⁴ Cho, H.⁵ Chung, J.H.⁶ Sok, D.E.⁷ Ahn, B.Z.⁸

10
- 0034056428
- Song, G. Y.; Kim, Y.; You, Y. J.; Cho, H.; Kim, S. H.; Sok, D. E.; Ahn, B. Z. Arch. Pharm. Pharm. Med. Chem., 2000, 333, 87.
- (2000) Arch. Pharm. Pharm. Med. Chem , vol.333 , pp. 87
- Song, G.Y.¹ Kim, Y.² You, Y.J.³ Cho, H.⁴ Kim, S.H.⁵ Sok, D.E.⁶ Ahn, B.Z.⁷

11
- 0023126508
- Terada, A.; Tanoue, Y.; Hatada, A.; Sakamoto, H. Bull. Chem. Soc. Jpn., 1987, 60, 205.
- (1987) Bull. Chem. Soc. Jpn , vol.60 , pp. 205
- Terada, A.¹ Tanoue, Y.² Hatada, A.³ Sakamoto, H.⁴

12
- 0030692127
- Couladouros, E. A.; Plyta, Z. F.; Strongilos, A. T.; Papageorgiou, V. P. Tetrahedron Lett., 1997, 38, 7263.
- (1997) Tetrahedron Lett , vol.38 , pp. 7263
- Couladouros, E.A.¹ Plyta, Z.F.² Strongilos, A.T.³ Papageorgiou, V.P.⁴

13
- 84986706391
- Braun, M.; Bauer, C. Liebigs Ann. Chem., 1991, 1157.
- (1991) Liebigs Ann. Chem , pp. 1157
- Braun, M.¹ Bauer, C.²

14
- 0036002150
- Lu, Q.; Duan, W. H.; Cai, J. C. Chinese Chem. Lett., 2002, 13, 113.
- (2002) Chinese Chem. Lett , vol.13 , pp. 113
- Lu, Q.¹ Duan, W.H.² Cai, J.C.³

15
- 0036269092
- Yang, H.; Li, Q.; Bao, J. X.; Lu. W.; Aisa, H. A.; Cai, J. C. Chinese Chem. Lett., 2002, 13, 515.
- (2002) Chinese Chem. Lett , vol.13 , pp. 515
- Yang, H.¹ Li, Q.² Bao, J.X.³ Lu, W.⁴ Aisa, H.A.⁵ Cai, J.C.⁶

16
- 0028841815
- Torii, S.; Akiyama, K.; Yamashita, H.; Inokuchi, T. Bull. Chem. Soc. Jpn., 1995, 68, 2917.
- (1995) Bull. Chem. Soc. Jpn , vol.68 , pp. 2917
- Torii, S.¹ Akiyama, K.² Yamashita, H.³ Inokuchi, T.⁴

17
- 0031954665
- Nicolaou, K. C.; Hepworth, D. Angew. Chem. Int. Ed., 1998, 37, 839.
- (1998) Angew. Chem. Int. Ed , vol.37 , pp. 839
- Nicolaou, K.C.¹ Hepworth, D.²

18
- 0037090424
- Couladouros, E. A.; Strongilos, A. T.; Papageorgiou, V. P.; Plyta, Z. F. Chem. Eur. J., 2002, 8, 1795.
- (2002) Chem. Eur. J , vol.8 , pp. 1795
- Couladouros, E.A.¹ Strongilos, A.T.² Papageorgiou, V.P.³ Plyta, Z.F.⁴

19
- 0001241577
- Barbot, F.; Miginiac, P. Tetrahedron Lett., 1975, 3829.
- (1975) Tetrahedron Lett , pp. 3829
- Barbot, F.¹ Miginiac, P.²

20
- 0032473441
- Hong, B. C.; Hong, J. H.; Tsai, Y. C. Angew. Chem. Int. Ed., 1998, 37, 468.
- (1998) Angew. Chem. Int. Ed , vol.37 , pp. 468
- Hong, B.C.¹ Hong, J.H.² Tsai, Y.C.³

21
- 0000162932
- Loh, T. P.; Zhou, J. R.; Yin, Z. Org. Lett., 1999, 1, 1855.
- (1999) Org. Lett , vol.1 , pp. 1855
- Loh, T.P.¹ Zhou, J.R.² Yin, Z.³

22
- 22144438294
- Cheng, H. S.; Loh, T. P. Pure Appl. Chem., 2005, 77, 1199.
- (2005) Pure Appl. Chem , vol.77 , pp. 1199
- Cheng, H.S.¹ Loh, T.P.²

23
- 0035982907
- Tsuji, T.; Usugi, S. I.; Yorimitsu, H.; Shinokubo, H.; Matsubara, S.; Oshima, K. Chem. Lett., 2002, 1, 2.
- (2002) Chem. Lett , vol.1 , pp. 2
- Tsuji, T.¹ Usugi, S.I.² Yorimitsu, H.³ Shinokubo, H.⁴ Matsubara, S.⁵ Oshima, K.⁶

24
- 33846653976
- Xu, D. F.; Guan, P. J.; Li, S. S. J. Chem. Res., 2006, 12, 779.
- (2006) J. Chem. Res , vol.12 , pp. 779
- Xu, D.F.¹ Guan, P.J.² Li, S.S.³

25
- 33750041945
- Jasti, R.; Rychnovsky, S. D. J. Am. Chem. Soc., 2006, 128, 13640.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 13640
- Jasti, R.¹ Rychnovsky, S.D.²

26
- 23644446275
- Barry, C. S.; Bushby, N.; Harding, J. R.; Hughes, R. A.; Parker, G. D.; Roe, R.; Willis, C. L. Chem. Commun., 2005, 3727.
- (2005) Chem. Commun , pp. 3727
- Barry, C.S.¹ Bushby, N.² Harding, J.R.³ Hughes, R.A.⁴ Parker, G.D.⁵ Roe, R.⁶ Willis, C.L.⁷

27
- 0013254056
- Marumoto, S.; Jaber, J. J.; Vitale, J. P.; Rychnovsky, S. D. Org. Lett., 2002, 4, 3919.
- (2002) Org. Lett , vol.4 , pp. 3919
- Marumoto, S.¹ Jaber, J.J.² Vitale, J.P.³ Rychnovsky, S.D.⁴

28
- 50149120907
- Procedure for the synthesis of 5 as follows: To a suspension of zinc (10 g, 1.54 mol) in dry THF (150 ml) was added 4-bromo-2-methyl-2-butene (8 ml, 0.07 mol, and the solution was stirred at room temperature for 2 h under N2. Then centrifuged the reaction mixture and kept under N2 for the following reaction. A solution of (2, 2.76 g, 0.01mol) in dry THF (40 ml) was added to a solution prenylzinc bromide prepared above. After stirring for 1 h at room temperature, HMPA (20 ml) was added and THF was distilled. Then the mixture was heated to 130°C for 10 h. A saturated solution of NH4Cl was added into the reaction mixture. The solution was extracted with ethyl acetate and washed with brine, dried and concentrated. The residue was purified by flash column chromatography (diethyl ether: hexane, 1: 2) to afford (4, 2.91g, 84% yield) as yellow oil. To a solution of (4, 1.73 g, 0.005mol) in acetonitrile (50 ml) was added drop
- 3OH+Na]+.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.