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A Versatile Synthesis of O-Desmethylangolensin Analogues from Methoxy-Substituted Benzoic Acids
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 Title & Authors
A Versatile Synthesis of O-Desmethylangolensin Analogues from Methoxy-Substituted Benzoic Acids
Hong, Hyo Jeong; Lee, Jae In;
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 Abstract
The synthesis of O-desmethylangolensin (O-DMA) analogues from methoxy-substituted benzoic acids was described. Treatment of methoxy-substituted benzoic acids with 2 equiv of ethyllithium afforded methoxypropiophenones, which were subsequently transformed to ethyl 2-(methoxyphenyl)propionates via 1,2-rearrangement of the methoxyphenyl group using in triethyl orthoformate. After hydrolysis with KOH, the 2-(methoxyphenyl)propionic acids were reacted with di-2-pyridyl carbonate to afford 2-pyridyl 2-(methoxyphenyl)propionates, which were acylated with methoxy-substituted phenylmagnesium bromides to give methoxy--methyldesoxybenzoins. The methoxy groups of these compounds were selectively or fully demethylated using boron tribromide to give diverse O-DMA analogues in high yields.
 Keywords
O-Desmethylangolensin;Condensation;Substitution;Rearrangement;Demethylation;
 Language
English
 Cited by
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1.
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 References
1.
(a) Rafii, F.; Davis, C.; Park, M.; Heinze, T. M.; Beger, R. D. Arch. Microbiol. 2003, 180, 11. crossref(new window)

2.
(b) Atkinson, C.; Frankenfeld, C. L.; Lampe, J. W. Exp. Bio. Med. 2005, 230, 155.

3.
(c) Frankenfeld, C. L. Adv. Nutr. 2011, 317.

4.
(d) Chandrasekharan, S.; Aglin, A. J. Steroids Hormon. Sci. 2013, 2157.

5.
(a) Schmitt, E.; Dekant, W.; Stopper, H. Toxicology in Vitro 2001, 15, 433. crossref(new window)

6.
(b) Frankenfeld, C. L.; McTiernan, A.; Aiello, E. J.; Thomas, W. K.; LaCroix, K.; Schramm, J.; Schwartz, S. M.; Holt, V. L.; Lampe, J. W. Cancer Epidemiol. Biomakers Prev. 2004, 13, 1156.

7.
(c) Kim, J.; Kim, H. J.; Joung, H.; Park, M. K.; Li, S.; Song, Y. J.; Franke, A. A.; Paik, H.-Y. British J. Nutr. 2010, 104, 709. crossref(new window)

8.
(a) L'homme, R.; Brouwers, E.; Al-Maharik, N.; Lapcik, O.; Hampl, R.; Mikola, H.; Wahala, K.; Adlercreutz, H. J. Steroid Biochem. Mol. Biol. 2002, 81, 353. crossref(new window)

9.
(b) Kuklenyik, Z.; Ye, X.; Reich, J. A.; Needham, L. L.; Calafat, A. M. J. Chromato. Sci. 2004, 42, 495. crossref(new window)

10.
(c) Grynkiewicz, G.; Ksycinska, H.; Ramza, J.; Zagrodzka, J. Acta Chromatographica 2005, 31.

11.
Gardana, C.; Canzi, E.; Simonetti, P. J. Chromato. B 2014, 953-954, 30. crossref(new window)

12.
Kinjo, J.; Tsuchihashi, R.; Morito, K.; Hirose, T.; Aomori, T.; Nagao, T.; Okabe, H.; Nohara, T.; Masamune, Y. Biol. Pharm. Bull. 2004, 27, 185. crossref(new window)

13.
Ohtomo, T.; Uehara, M.; Penalvo, J. L.; Adlercreutz, H.; Katsumata, S.; Suzuki, K.; Takeda, K.; Masuyama, R.; Ishimi, Y. Eur. J. Nutr. 2008, 47, 273. crossref(new window)

14.
(a) Goto, H.; Terao, Y.; Akai, S. Chem. Pharm. Bull. 2009, 57, 346. crossref(new window)

15.
(b) Kelly, G. E.; Joannou, G. E. US patent 0286150 A1, 2006.

16.
Yokoyama, S.; Niwa, T.; Osawa, T.; Suzuki, T. Arch. Microbiol. 2010, 192, 15. crossref(new window)

17.
(a) Choi, E. J.; Lee, J. I.; Kim, G. H. Int. J. Mol. Med. 2013, 31, 726.

18.
(b) Choi, E. J.; Kim, G. H. Oncology Lett. 2013, 6, 1784.

19.
Bannwart, C.; Adlercreutz, H.; Fotsis, T.; Wahala, K.; Hase, T.; Brunow, G. Finn. Chem. Lett. 1984, 120.

20.
Thakur, V. V.; Sudalai, A. Indian J. Chem. 2005, 44B, 557.

21.
(a) Kenyon, W. G.; Meyer, R. B.; Hauser, C. R. J. Org. Chem. 1963, 28, 3108. crossref(new window)

22.
(b) Rieu, J.-P.; Boucherle, A.; Cousse, H.; Mouzin, G. Tetrahedron 1986, 42, 4095. crossref(new window)

23.
(c) Silva, A. M.; Silva, C. O.; Barbosa, A. G. H.; Fontes, R. A.; Pinheiro, S.; Lima, M. E. F.; Castro, R. N. J. Braz. Chem. Soc. 2011, 22, 756. crossref(new window)

24.
(a) Oldfield, M. F.; Chen, L.; Botting, N. P. Tetrahedron 2004, 60, 1887. crossref(new window)

25.
(b) Gupta, A.; Ray, S. Synthesis 2008, 3783.

26.
Whalley, J. L.; Oldfield, M. F.; Botting, N. P. Tetrahedron 2000, 56, 455. crossref(new window)

27.
Jain, A. C.; Paliwar, P. Indian J. Chem. 1988, 27B, 985.

28.
Hakala, U.; Wahala, K. Tetrahedron Lett. 2006, 47, 8375. crossref(new window)

29.
Snape, T. J. Synlett 2008, 2689.

30.
(a) Wahala, K.; Salakka, A.; Adlercreutz, H. Proc. Soc. Exp. Biol. Med. 1998, 217, 293. crossref(new window)

31.
(b) Salakka, A.; Wahala, K. J. Chem. Soc. Perkin Trans. 1 1999, 2601.

32.
Salakka, A. K.; Jokela, T. H.; Wahala, K. Beilstein J. Org. Chem. 2006, 2, 16. crossref(new window)

33.
Nongkhlaw, R. L.; Nongrum, R.; Nongkynrih, I.; Vattakunnel, F. M.; Myrboh, B. Indian J. Chem. 2005, 44B, 1054.

34.
Paquette, L. A., Ed. Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons: New York, U. S. A., 1995; Vol. 4, p 2274.

35.
Wahala, K.; Jokela, T.; Salakka, A.; Kaltia, S.; Mesilaakso, M. J. Chem. Soc. Perkin Trans. 1 2001, 642.