DOI QR코드

DOI QR Code

First Total Synthesis of Prorepensin with a Bis-Geranylated Chalcone

  • Jung, Eun-Mi (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Lee, Yong-Rok (School of Chemical Engineering and Technology, Yeungnam University)
  • Published : 2009.11.20

Abstract

The first total synthesis of naturally occurring prorepensin with a bis-geranylated chalcone has been achieved by a convergent sequence. The key strategy involved in the synthesis of prorepensin was chalcone formation by aldol condensation of the corresponding geranylated acetophenone with geranylated benzaldehyde.

Keywords

References

  1. Kumazawa, S.; Ueda, R.; Hamasaka, T.; Fukumoto, S.; Fujimoto, T.; Nakayama, T. J. Agric. Food Chem. 2007, 55, 7722. https://doi.org/10.1021/jf071187h
  2. Miranda, C. L.; Stevens, J. F.; Ivanov, V.; McCall, M.; Frei, B.; Deinzer, M. L.; Buhler, D. R. J. Agric. Food Chem. 2000, 48, 3876. https://doi.org/10.1021/jf0002995
  3. Vogel, S.; Heilmann, J. J. Nat. Prod. 2008, 71, 1237. https://doi.org/10.1016/j.phytochem.2004.03.033
  4. Rodriguez, R. J.; Miranda, C. L.; Stevens, J. F.; Deinzer, M. L.; Buhler, D. R. Food Chem. Toxicol. 2001, 39, 437. https://doi.org/10.1002/ijc.11256
  5. Chi, Y. S.; Jong, H. G.; Son, K. H.; Chang, H. W.; Kang, S. S.; Kim, H. P. Biochem. Pharmacol. 2001, 62, 1185. https://doi.org/10.1055/s-2004-815537
  6. Miranda, C. L.; Aponso, G. L. M.; Stevens, J. F.; Deinzer, M. L.; Buhler, D. R. Cancer Lett. 2000, 149, 21 https://doi.org/10.1021/np058080d
  7. Inamori, Y.; Baba, K.; Tsujibo, H.; Taniguchi, M.; Nakata, K.; Kozawa, M. Chem. Pharm. Bull. 1991, 39, 1604 https://doi.org/10.1248/cpb.39.1604
  8. Jayasinghe, L.; Balasooriya, B. A. I. S.; Padmini, W. C.; Hara, N.; Fujimoto, Y. Phytochemistry 2004, 65, 1287 https://doi.org/10.1016/j.phytochem.2004.03.033
  9. Kimura, Y.; Baba, K. Int. J. Cancer 2003, 106, 429 https://doi.org/10.1021/jf070720q
  10. Kimura, Y. Taniguchi, M.; Baba, K. Planta Med. 2004, 70, 211 https://doi.org/10.2174/1385272003375905
  11. Akihisa, T.; Tokuda, H.; Hasegawa, D.; Ukiya, M.; Kimura, Y.; Enjo, F.; Suzuki, T.; Nishino, H. J. Nat. Prod. 2006, 69, 38 https://doi.org/10.1021/np058080d
  12. Rosselli, S.; Bruno, M.; Maggio, A.; Bellone, G.; Formisano, C.; Mattia, C. A.; Di Micco, S.; Bifulco, G. Eur. J. Org. Chem. 2007, 2504
  13. Murakami, S.; Kijima, H.; Isobe, Y.; Muramatsu, M.; Aihara, H.; Otomo, S.; Baba, K.; Kozawa, M. J. Pharm. Pharmacol. 1990, 42, 723 https://doi.org/10.1021/jo800367r
  14. Enoki, T.; Ohnogi, H.; Nagamine, K.; Kudo, Y.; Sugiyama, K.; Tanabe, M.; Kobayashi, E.; Sagawa, H.; Kato, I. J. Agric. Food Chem. 2007, 55, 6013 https://doi.org/10.1021/np980026s
  15. Abegaz, B. M.; Ngadjui, B. T.; Dongo, E.; Bezabih, M.-T. Curr. Org. Chem. 2000, 4, 1079 https://doi.org/10.1021/jo8015924
  16. Nikaido, T.; Ohmoto, T.; Kinoshita, T.; Sankawa, U.; Delle Monache, F.; Botta, B.; Tomimori, T.; Miyaichi, Y.; Shirataki, Y.; Yokoe, I.; Komatsu, M. Chem. Pharm. Bull. 1989, 37, 1392 https://doi.org/10.1002/adsc.200303203
  17. Abegaz, B. M.; Ngadjui, B. T.; Dongo, E.; Ngameni, B.; Nindi, M. N.; Bezabih, M. Phytochemistry 2002, 59, 877.
  18. Vouffo, B.; Hussain, H.; Eyong, K. O.; Dongo, E.; Folefoc, G. N.; Nkengfack, A. E.; Krohn, K. Biochem. System. Ecol. 2008, 36, 730 https://doi.org/10.1016/j.bse.2008.06.004
  19. Lee, Y. R.; Li, X.; Kim, J. H. J. Org. Chem. 2008, 73, 4313. https://doi.org/10.1021/jo800367r
  20. Lee, Y. R.; Xia, L. Synthesis 2007, 3240.
  21. Lee, Y. R.; Kim, D. H. Synthesis 2006, 603
  22. Huang, C.; Zhang, Z.; Li, Y. J. Nat. Prod. 1998, 61, 1283 https://doi.org/10.1021/np980026s
  23. Boukouvalas, J.; Loach, R. P. J. Org. Chem. 2008, 73, 8109 https://doi.org/10.1021/jo8015924
  24. Tohma, H.; Kita, Y. Adv. Synth. Catal. 2004, 346, 111 https://doi.org/10.1002/adsc.200303203

Cited by

  1. Selective Prenylation of Protected Phenols for Synthesis of Pawhuskin A Analogues vol.81, pp.4, 2009, https://doi.org/10.1021/acs.joc.5b02756
  2. Secondary metabolites, their structural diversity, bioactivity, and ecological functions: An overview vol.4, pp.6, 2009, https://doi.org/10.1515/psr-2018-0100
  3. Secondary metabolites, their structural diversity, bioactivity, and ecological functions: An overview vol.4, pp.6, 2009, https://doi.org/10.1515/psr-2018-0100