Synthesis of dihydrodehydrodiconiferyl alcohol: The revised structure of lawsonicin

Organic and Biomolecular Chemistry

Volumn 8, Issue 1, 2010, Pages 107-113

  Meng, Junxiu ^a,b   Jiang, Tao ^b   Bhatti, Huma Aslam ^c   Siddiqui, Bina S ^c   Dixon, Sally ^a   Kilburn, Jeremy D ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b OCEAN UNIVERSITY OF CHINA   (China)

^c UNIVERSITY OF KARACHI   (Pakistan)

Author keywords

[No Author keywords available]

Indexed keywords

POSITIVE IONS;

C-H INSERTION; CONCISE SYNTHESIS; NATURAL PRODUCTS; NATURALLY OCCURRING; NEOLIGNAN; SPECTRAL DATA;

CHEMISTRY;

LAWSONIA INERMIS;

EID: 76849100007     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b918179b     Document Type: Article

References (47)

1. B. S. Siddiqui, M. N. Kardar, S. T. Ali and S. Khan, Helv. Chim. Acta, 2003, 86, 2164.
2. 9) precursors has been advanced; however, to our knowledge, the requisite 4-(3-hydroxypropyl)-substituted cinnamyl alcohol precursor, for lawsonicin biosynthesis according to this pathway, has not been identified. See: (a) L. Jurd, G. Manners and K. Stevens, J. Chem. Soc. Chem. Commun., 1972, 992;
3. (b) W. D. Ollis and O. R. Gottlieb, Chem. Commun. (London), 1968, 1396.
4. L. B. Davin, M. Jourdes, A. M. Patten, K-W. Kim, D. G. Vassao and N. G. Lewis, Nat. Prod. Rep., 2008, 25, 1015.
5. M. Sefkow, Synthesis, 2003, 2595.
6. (a) H. Erdtman, Justus Liebigs Ann. Chem. 1933, 503, 283;
7. (b) N. G. Lewis, L. B. Davin, Lignin and Lignan Biosynthesis, ACS Symposium Series, ed. N. G. Lewis and S. Sarkanen, American Chemical Society, Washington DC, USA, 1998, 697, 334.
8. T. Shiba, L. Xiao, T. Miyakoshi and C. L. Chen, J. Mol. Catal. B: Enzym., 2000, 10, 605.
9. (a) S. Y. Guan, J. Mlynař and S. Sarkanen, Phytochemistry, 1997, 45, 911;
10. (b) K. Syrjänen and G Brunow, J. Chem. Soc. Perkin Trans. 1, 1998, 3425-3429.
11. (a) S. R. Angle and J. D. Rainier, J. Org. Chem. 1992, 57, 6883;
12. (b) S. R. Angle and K. D. Turnbull, J. Am. Chem. Soc. 1990, 112, 3698;
13. (c) S. R. Angle and K. D. Turnbull, J. Org. Chem. 1993, 58, 5360.
14. For examples of 1,6-nucleophilic addition to quinone methide derivatives in biomimetic neolignan syntheses, see: (a) S. Antus, R. Bauer, A. Gottsegen, O. Seligmann and H. Wagner, Liebigs Ann. Chem. 1987, 357;
15. (b) L. Juhász, L. Kurd and S. Antus, J. Nat. Prod., 2000, 63, 866.
16. To our knowledge, presumed reductase catalysis of this transformation has not yet been specified. For a discussion of the overall oxidoreductive biosynthesis, see: M. Nose, M. A. Bernards, M. Furlan, J. Zajíček, T L. Eberhardt and N G Lewis, Phytochemistry, 1995, 39, 71.
17. (a) P. K. Agrawal, S. K. Agarwal and R. P. Rastogi, Phytochemistry, 1980, 19, 1260;
18. (b) J. M. Fang, C. K. Lee and Y. S. Cheng, Phytochemistry, 1992, 31, 3659;
19. (c) A. Jutiviboonsuk, H. Zhang, G. T Tan, C. Ma, N. Van Hung, N. M. Cuong, N. Bunyapraphatsara, D. D. Soejarto and H. H. S. Fong, Phytochemistry, 2005, 66, 2745;
20. d) S. Kawai, K. Sugishita and H. Ohashi, Phytochemistry, 1999, 51, 243;
21. (e) M. Ono, Y. Nishida, C. Masuoka, J.-C. Li, M. Okawa, T. Ikeda and T. Nohara, J.Nat. Prod., 2004, 67, 2073.
22. P. M. Pauletti, A. R. Araújo, M. C. M. Young, A. M. Giesbrecht and V. D. Bolzani, Phytochemistry, 2000, 55, 597.
23. (a) T. Deyama, T. Ikawa, S. Kitagawa and S. Nishibe, Chem. Pharm. Bull., 1987, 35, 1785;
24. b) W.-L. Lo, Y-C Wu, T.-J. Hsieh, S.-H. Kuo, H.-C. Lin and C.-Y. Chen, Chin. Pharm. J., 2004, 56, 69;
25. (c) V. Seidel, F. Bailleul and P. G. Waterman, J. Nat. Prod., 2000, 63, 6.
26. Y. Fukuyama, M. Nakahara, H. Minami and M. Kodama, Chem. Pharm. Bull., 1996, 44, 1418.
27. For elucidation of the 2,3-trans-configuration of dihydrodehydrodiconiferyl alcohol, see: ref. 13 and 14.
28. 13CH-6 = 111.9 ppm: D. L. J. Clive, S. P. Fletcher and M. Z. Zhu, Chem. Commun., 2003,
29. 13CH-7 = 94.1 ppm: J. W Benbow and R. Katoch-Rouse, J. Org. Chem. 2001, 66, 4965.
30. Data reproduced in Table 1 is from the isolated natural product, see: ref. 14. Corresponding data and structural verification has been reported for synthetic rac-trans-2, see: L. Pieters, S. Van Dyck, M. Gao, R. Bai, E. Hamel, A. Vlietinck and G. Lemiere, J Med. Chem. 1999, 42, 5475.
31. B. Sen, J. Am. Chem. Soc. 1952, 74, 3445.
32. (a) M. Cabrera, M. Simoens, G. Falchi, M. L. Lavaggi, O. E. Piro, E. E. Castellano, A. Vidal, A. Azqueta, A. Monge, A. L. de Cerain, G. Sagrera, G. Scoane, H. Cerecetto and M. Gonzalez, Bioorg. Med. Chem. 2007, 15, 3356;
33. (b) C. X. Qin, X. Q. Chen, R. A. Hughes, S. J. Williams and O. L. Woodman, J. Med. Chem. 2008, 51,1874.
34. M. S. Khanna, O. V. Singh, C. P. Garg and R. P. Kapoor, Synth. Commun., 1993, 23, 585.
35. H2,H3(rac)cis-isomer = 10.0 Hz: L. Juhasz, L. Szilagyi, S. Antus, J. Visy, F. Zsila and M. Simonyi, Tetrahedron, 2002, 58, 4261.
36. L. Pieters, T. Debruyne, A. Degroot, G. Mei, R. Dommisse, G. Lemiere and A. Vlietinck, Magn. Reson. Chem. 1993, 31, 692.
37. S. García-Muñoz, M. Alvarez-Corral, L. Jimenez-Gonzalez, C LopezSanchez, A. Rosales, M. Munoz-Dorado and I. Rodriguez-Garcia, Tetrahedron, 2006, 62, 12182.
38. H. M. L. Davies, W. R. Cantrell, K. R. Romines and J. S. Baum, Org. Synth., 1991, 70, 93.
39. H. M. L. Davies, M. V. A. Grazini and E. Aouad, Org. Lett., 2001, 3, 1475.
40. 4-mediated intramolecular C-H insertion in 2,3-dihydroxybenzofuran natural product synthesis, see: (a) W. Kurosawa, T. Kan and T. Fukuyama, Synlett, 2003, 7, 1028;
41. (b) W. Kurosawa, H. Kobayashi, T. Kan and T Fukuyama, Tetrahedron, 2004, 60, 9615.
42. H. Saito, H. Oishi, S. Kitagaki, S. Nakamura, M. Anada and S. Hashimoto, Org. Lett., 2002, 4, 3887.
43. B. M. Trost and J. Xie, J. Am. Chem. Soc. 2006, 128, 6044.
44. S. Y. Lin, C. L. Chen and Y. J. Lee, J. Org. Chem. 2003, 68, 2968.
45. 4/THF reducing conditions at -60 °C, has been reported, see: ref. 32.
46. J. W. Bode, M. P. Doyle, M. N. Protopova and Q.-L. Zhou, J. Org. Chem. 1996, 61, 9146.
47. S. García-Muñoz, L. Jimenez-Gonzalez, M. Alvarez-Corral, M. Munoz-Dorado and I. Rodriguez-Garcia, Synlett, 2005, 3011.