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Tetrahedron Letters

Volumn 54, Issue 39, 2013, Pages 5322-5324

Synthesis of 4-benzyl-3-phenylbutenolide natural products

(3) Parker, Anna N a Lock, Matthew J a Hutchison, John M a

a AUBURN UNIVERSITY AT MONTGOMERY (United States)

Author keywords

Eutypoid A; Gymnoascolide A; Mannich type amino alkylation; Microperfuranone; Suzuki coupling

Indexed keywords

4 BENZYL 3 PHENYLBUTENOLIDE; FURANONE DERIVATIVE; GYMNOASCOLIDE A; MICROPERFURANONE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; DRUG SYNTHESIS; MANNICH REACTION; RACEMIZATION; RING OPENING; SUZUKI REACTION;

EID: 84883055727 PISSN: 00404039 EISSN: 18733581 Source Type: Journal
DOI: 10.1016/j.tetlet.2013.07.101 Document Type: Article

Times cited : (11)

References (38)

1
- 0031795852
- H. Fujimoto, Y. Satoh, K. Yamaguchi, and M. Yamazaki Chem. Pharm. Bull. 46 1998 1506 1510
- (1998) Chem. Pharm. Bull. , vol.46 , pp. 1506-1510
- Fujimoto, H.¹ Satoh, Y.² Yamaguchi, K.³ Yamazaki, M.⁴

2
- 33645549964
- H. Fujimoto, A. Takeshi, Y.-P. Kim, and M. Ishibashi Chem. Pharm. Bull. 54 2006 550 553
- (2006) Chem. Pharm. Bull. , vol.54 , pp. 550-553
- Fujimoto, H.¹ Takeshi, A.² Kim, Y.-P.³ Ishibashi, M.⁴

3
- 33747379476
- A. Kralj, S. Kehraus, A. Krick, E. Eguereva, G. Kelter, M. Maurer, A. Wortmann, H.-H. Fiebig, and G.M. Konig J. Nat. Prod. 69 2006 995 1000
- (2006) J. Nat. Prod. , vol.69 , pp. 995-1000
- Kralj, A.¹ Kehraus, S.² Krick, A.³ Eguereva, E.⁴ Kelter, G.⁵ Maurer, M.⁶ Wortmann, A.⁷ Fiebig, H.-H.⁸ Konig, G.M.⁹

4
- 24744444493
- B. Clark, R.J. Capon, E. Lacey, S. Tennant, J.H. Gill, B. Bulheller, and G. Bringmann J. Nat. Prod. 68 2005 1226 1230
- (2005) J. Nat. Prod. , vol.68 , pp. 1226-1230
- Clark, B.¹ Capon, R.J.² Lacey, E.³ Tennant, S.⁴ Gill, J.H.⁵ Bulheller, B.⁶ Bringmann, G.⁷

5
- 28444457802
- T. Hosoe, T. Iizuka, S.-I. Komai, D. Wakana, T. Itabashi, K. Nozawa, K. Fukushima, and K.-I. Kawai Phytochemistry 66 2005 2776 2779
- (2005) Phytochemistry , vol.66 , pp. 2776-2779
- Hosoe, T.¹ Iizuka, T.² Komai, S.-I.³ Wakana, D.⁴ Itabashi, T.⁵ Nozawa, K.⁶ Fukushima, K.⁷ Kawai, K.-I.⁸

6
- 0036650985
- Y. Lin, H. Li, G. Jiang, S. Zhou, L.L.P. Vrijmoed, and E.B.G. Jones Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 41 2002 1542 1544
- (2002) Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. , vol.41 , pp. 1542-1544
- Lin, Y.¹ Li, H.² Jiang, G.³ Zhou, S.⁴ Vrijmoed, L.L.P.⁵ Jones, E.B.G.⁶

7
- 79951536560
- D. Schulz, B. Ohlendorf, H. Zinecker, R. Schmaljohann, and J.F. Imhoff J. Nat. Prod. 74 2011 99 101
- (2011) J. Nat. Prod. , vol.74 , pp. 99-101
- Schulz, D.¹ Ohlendorf, B.² Zinecker, H.³ Schmaljohann, R.⁴ Imhoff, J.F.⁵

8
- 0032897489
- A. Soriente, M. De Rosa, A. Scettri, G. Sodano, M.C. Terencio, M. Paya, and M.J. Alcaraz Curr. Med. Chem. 6 1999 415 431
- (1999) Curr. Med. Chem. , vol.6 , pp. 415-431
- Soriente, A.¹ De Rosa, M.² Scettri, A.³ Sodano, G.⁴ Terencio, M.C.⁵ Paya, M.⁶ Alcaraz, M.J.⁷

9
- 25844527321
- Y. Yamano, Y. Mizuguchi, Y. Fujita, M. Yoshida, M. Ito, K. Nakagawa, and T. Okano Bioorg. Med. Chem. 13 2005 6002 6008
- (2005) Bioorg. Med. Chem. , vol.13 , pp. 6002-6008
- Yamano, Y.¹ Mizuguchi, Y.² Fujita, Y.³ Yoshida, M.⁴ Ito, M.⁵ Nakagawa, K.⁶ Okano, T.⁷

10
- 58449114054
- M.C. Monti, A. Casapullo, C.N. Cavasotto, A. Tosco, F.D. Piaz, A. Zeimys, L. Margarucci, and R. Riccio Chem. Eur. J. 15 2009 1155 1163
- (2009) Chem. Eur. J. , vol.15 , pp. 1155-1163
- Monti, M.C.¹ Casapullo, A.² Cavasotto, C.N.³ Tosco, A.⁴ Piaz, F.D.⁵ Zeimys, A.⁶ Margarucci, L.⁷ Riccio, R.⁸

11
- 77649213543
- S.S. Ebada, W.H. Lin, and P. Proksch Mar. Drugs 8 2010 313 346
- (2010) Mar. Drugs , vol.8 , pp. 313-346
- Ebada, S.S.¹ Lin, W.H.² Proksch, P.³

12
- 77952961509
- R. De Simone, R.M. Andres, M. Aquino, I. Bruno, M.D. Guerrero, M.C. Terencio, M. Paya, and R. Riccio Chem. Biol. Drug Des. 76 2010 17 24
- (2010) Chem. Biol. Drug Des. , vol.76 , pp. 17-24
- De Simone, R.¹ Andres, R.M.² Aquino, M.³ Bruno, I.⁴ Guerrero, M.D.⁵ Terencio, M.C.⁶ Paya, M.⁷ Riccio, R.⁸

13
- 84864443266
- R. De Simone, I. Bruno, R. Riccio, K. Stradler, J. Bauer, A.M. Schaible, S. Laufer, and O. Werz Bioorg. Med. Chem. 20 2012 5012 5016
- (2012) Bioorg. Med. Chem. , vol.20 , pp. 5012-5016
- De Simone, R.¹ Bruno, I.² Riccio, R.³ Stradler, K.⁴ Bauer, J.⁵ Schaible, A.M.⁶ Laufer, S.⁷ Werz, O.⁸

14
- 0035477020
- S. Frame, and P. Cohen Biochem. J. 359 2001 1 16
- (2001) Biochem. J. , vol.359 , pp. 1-16
- Frame, S.¹ Cohen, P.²

15
- 0034859101
- C.A. Grimes, and R.S. Jope Prog. Neurobiol. 65 2001 391 426
- (2001) Prog. Neurobiol. , vol.65 , pp. 391-426
- Grimes, C.A.¹ Jope, R.S.²

16
- 0037383322
- B.W. Doble, and J.R. Woodgett J. Cell Sci. 116 2003 1175 1186
- (2003) J. Cell Sci. , vol.116 , pp. 1175-1186
- Doble, B.W.¹ Woodgett, J.R.²

17
- 33947597084
- R.S. Jope, C.J. Yuskaitis, and E. Beurel Neurochem. Res. 32 2007 577 595
- (2007) Neurochem. Res. , vol.32 , pp. 577-595
- Jope, R.S.¹ Yuskaitis, C.J.² Beurel, E.³

18
- 39849110726
- C. Hooper, R. Killick, and S. Lovestone J. Neurochem. 104 2008 1433 1439
- (2008) J. Neurochem. , vol.104 , pp. 1433-1439
- Hooper, C.¹ Killick, R.² Lovestone, S.³

19
- 57349143530
- J. Luo Cancer Lett. 273 2009 194 200
- (2009) Cancer Lett. , vol.273 , pp. 194-200
- Luo, J.¹

20
- 0036799220
- I. Dorronsoro, A. Castro, and A. Martinez Expert Opin. Ther. Pat. 12 2002 1527 1536
- (2002) Expert Opin. Ther. Pat. , vol.12 , pp. 1527-1536
- Dorronsoro, I.¹ Castro, A.² Martinez, A.³

21
- 3042635178
- P. Cohen, and M. Goedert Nat. Rev. Drug Disc. 3 2004 479 487
- (2004) Nat. Rev. Drug Disc. , vol.3 , pp. 479-487
- Cohen, P.¹ Goedert, M.²

22
- 4344619713
- L. Meijer, M. Flajolet, and P. Greengard Trends Pharmacol. Sci. 25 2004 471 480
- (2004) Trends Pharmacol. Sci. , vol.25 , pp. 471-480
- Meijer, L.¹ Flajolet, M.² Greengard, P.³

23
- 34548201878
- P. Merino, T. Tejero, J.I. Delso, and R. Matute Curr. Org. Chem. 11 2007 1076 1091
- (2007) Curr. Org. Chem. , vol.11 , pp. 1076-1091
- Merino, P.¹ Tejero, T.² Delso, J.I.³ Matute, R.⁴

24
- 51649086878
- T. Montagnon, M. Tofi, and G. Vassilikogiannakis Acc. Chem. Res. 41 2008 1001 1011
- (2008) Acc. Chem. Res. , vol.41 , pp. 1001-1011
- Montagnon, T.¹ Tofi, M.² Vassilikogiannakis, G.³

25
- 76749137955
- L.A. Badovskaya, and L.V. Povarova Chem. Heterocycl. Compd. 45 2009 1023 1034
- (2009) Chem. Heterocycl. Compd. , vol.45 , pp. 1023-1034
- Badovskaya, L.A.¹ Povarova, L.V.²

26
- 0000604444
- J.J. Bourguignon, and C.G. Wermuth J. Org. Chem. 46 1981 4889 4894
- (1981) J. Org. Chem. , vol.46 , pp. 4889-4894
- Bourguignon, J.J.¹ Wermuth, C.G.²

27
- 0023949079
- J.J. Bourguignon, A. Schoenfelder, M. Schmitt, C.G. Wermuth, V. Helcher, B. Charlier, and M. Maitre J. Med. Chem. 31 1988 893 897
- (1988) J. Med. Chem. , vol.31 , pp. 893-897
- Bourguignon, J.J.¹ Schoenfelder, A.² Schmitt, M.³ Wermuth, C.G.⁴ Helcher, V.⁵ Charlier, B.⁶ Maitre, M.⁷

28
- 0042693206
- G. Hughes, M. Kimura, and S.L. Buchwald J. Am. Chem. Soc. 125 2003 11253 11258
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 11253-11258
- Hughes, G.¹ Kimura, M.² Buchwald, S.L.³

29
- 17444395217
- Microperfuranone synthesis: D.J. Clive, Minaruzzaman, and L. Ou J. Org. Chem. 70 2005 3318 3320
- (2005) J. Org. Chem. , vol.70 , pp. 3318-3320
- Clive, D.J.¹ Minaruzzaman² Ou, L.³

30
- 38349160511
- Gymnoascolide A synthesis: M.M. Baag, and N.P. Argada Synthesis 2008 26 28
- (2008) Synthesis , pp. 26-28
- Baag, M.M.¹ Argada, N.P.²

31
- 0032532518
- For the synthesis of 3-aryl and 4-aryl-2(5H)-furanones via Suzuki coupling reaction, see: J. Boukouvalas, N. Lachance, M. Ouellet, and M. Trudeau Tetrahedron Lett. 39 1998 7665 7668
- (1998) Tetrahedron Lett. , vol.39 , pp. 7665-7668
- Boukouvalas, J.¹ Lachance, N.² Ouellet, M.³ Trudeau, M.⁴

32
- 0037060937
- F. Bellina, C. Anselmi, and R. Rossi Tetrahedron Lett. 43 2002 2023 2027
- (2002) Tetrahedron Lett. , vol.43 , pp. 2023-2027
- Bellina, F.¹ Anselmi, C.² Rossi, R.³

33
- 0037069717
- J. Zhang, P.G. Blazecka, D. Belmont, and J.G. Davidson Org. Lett. 4 2002 4559 4561
- (2002) Org. Lett. , vol.4 , pp. 4559-4561
- Zhang, J.¹ Blazecka, P.G.² Belmont, D.³ Davidson, J.G.⁴

34
- 0037716269
- F. Bellina, C. Anselmi, F. Martina, and R. Rossi Eur. J. Org. Chem. 12 2003 2290 2320
- (2003) Eur. J. Org. Chem. , vol.12 , pp. 2290-2320
- Bellina, F.¹ Anselmi, C.² Martina, F.³ Rossi, R.⁴

35
- 14644442893
- C.J. Mathews, J. Taylor, M.J. Tyte, and P.A. Worthington Synlett 2005 538 540
- (2005) Synlett , pp. 538-540
- Mathews, C.J.¹ Taylor, J.² Tyte, M.J.³ Worthington, P.A.⁴

36
- 33748413288
- Y.S. Song, Y.-J. Lee, B.T. Kim, and J.-N. Heo Tetrahedron Lett. 47 2006 7427 7430
- (2006) Tetrahedron Lett. , vol.47 , pp. 7427-7430
- Song, Y.S.¹ Lee, Y.-J.² Kim, B.T.³ Heo, J.-N.⁴

37
- 34848812555
- The naturally derived microperfuranone (1) is optically active: [ α ] D 21 = -6.8 (c 0.60, MeOH) (Ref. 1a). However, individual enantiomers of γ-hydroxybutenolides are known to undergo inter-conversion via open-chain tautomers.: W.H. Miles, D.G. Duca, B.R. Selfridge, C.A.P. De Sousa, K.B. Hamman, E.O. Goodzeit, and J.T. Freedman Tetrahedron Lett. 48 2007 7809 7812
- (2007) Tetrahedron Lett. , vol.48 , pp. 7809-7812
- Miles, W.H.¹ Duca, D.G.² Selfridge, B.R.³ De Sousa, C.A.P.⁴ Hamman, K.B.⁵ Goodzeit, E.O.⁶ Freedman, J.T.⁷

38
- 0033601203
- P.R. Brooks, M.C. Wirtz, M.G. Vetelino, D.M. Rescek, G.F. Woodworth, B.P. Morgan, and J.W. Coe J. Org. Chem. 64 1999 9719 9721
- (1999) J. Org. Chem. , vol.64 , pp. 9719-9721
- Brooks, P.R.¹ Wirtz, M.C.² Vetelino, M.G.³ Rescek, D.M.⁴ Woodworth, G.F.⁵ Morgan, B.P.⁶ Coe, J.W.⁷

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