Bulletin of the Korean Chemical Society

  • 제29권6호
  • /
  • Pages.1199-1204
  • /
  • 2008
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

First Concise Total Syntheses of Biologically Interesting Nicolaioidesin C, Crinatusin C1, and Crinatusin C2

  • Jung, Eun-Mi (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Lee, Yong-Rok (School of Chemical Engineering and Technology, Yeungnam University)
  • 발행 : 2008.06.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

The efficient and concise total syntheses of naturally occurring dihydrochalcone nicolaioidesin C, crinatusin C1, and crinatusin $C_2$ have been achieved from the readily available 2,6-dihydroxy-4-methoxyacetophenone and 2,4-dihydroxy-6-methoxyacetophenone. The key steps in the synthetic strategy were aldol reaction and Diels-Alder reaction.

키워드

참고문헌

  1. Win, N. N.; Awale, S.; Esumi, H.; Tezuka, Y.; Kadota, S. J. Nat. Prod. 2007, 70, 1582 https://doi.org/10.1021/np070286m
  2. Wang, Y.; Deng, T.; Lin, L.; Pan, Y.; Zheng, X. Phytother. Res. 2006, 20, 1052 https://doi.org/10.1002/ptr.1990
  3. Tuchinda, P.; Reutrakul, V.; Claeson, P.; Pongprayoon, U.; Sematong, T.; Santisuk, T.; Taylor, W. C. Phytochemistry 2002, 59, 169 https://doi.org/10.1016/S0031-9422(01)00451-4
  4. Trakoontivakorn, G.; Nakahara, K.; Shinmoto, H.; Takenaka, M.; Onishi-Kameyama, M.; Ono, H.; Yoshida, M.; Nagata, T.; Tsushida, T. J. Agric. Food Chem. 2001, 49, 3046 https://doi.org/10.1021/jf010016o
  5. Shindo, K.; Kato, M.; Kinoshita, A.; Kobayashi, A.; Koike, Y. Biosci. Biotechnol. Biochem. 2006, 70, 2281 https://doi.org/10.1271/bbb.60086
  6. Kirana, C.; Jones, G. P.; Record, I. R.; McIntosh, G. H. J. Nat. Med. 2007, 61, 131 https://doi.org/10.1007/s11418-006-0100-0
  7. Kiat, T. S.; Pippen, R.; Yusof, R.; Ibrahim, H.; Khalid, N.; Rahman, N. A. Bioorg. Med. Chem. Lett. 2006, 16, 3337 https://doi.org/10.1016/j.bmcl.2005.12.075
  8. Yun, J.-M.; Kweon, M.-H.; Kwon, H.; Hwang, J.-K.; Mukhtar, H. Carcinogenesis 2006, 27, 1454 https://doi.org/10.1093/carcin/bgi348
  9. Son, J. H.; Han, K.-L.; Lee, S.-H.; Hwang, J.-K. Biol. Pharm. Bull. 2005, 28, 1083 https://doi.org/10.1248/bpb.28.1083
  10. Tuntiwachwuttikul, P.; Pancharoen, O.; Reutrakul, V.; Byrne, L. T. Aust. J. Chem. 1984, 37, 449 https://doi.org/10.1071/CH9840449
  11. Cheenpracha, S.; Karalai, C.; Ponglimanont, C.; Subhadhirasakul, S.; Tewtrakul, S. Bioorg. Med. Chem. Lett. 2006, 14, 1710 https://doi.org/10.1016/j.bmc.2005.10.019
  12. Kress, W. J.; DeFilipps, R. A.; Farr, E.; Kyi, Y. Y. A Checklist of the Trees, Shrubs, Herbs, and Climbers of Myanmar in Contributions from the United States National Herbarium; Department of Systematic Biology-Botany, Natioal Museum of Natural History: Washington, DV, 2003; Vol. 45; p 120
  13. Hwang, J. K.; Chung, J. Y.; Baek, N. I.; Park, J. H. Int. J. Antimicrob. Agents 2004, 23, 377 https://doi.org/10.1016/j.ijantimicag.2003.08.011
  14. Yun, J.-M.; Kwon, H.; Hwang, J.-K. Planta Med. 2003, 69, 1102 https://doi.org/10.1055/s-2003-45190
  15. Panthong, A.; Tassaneeyakul, W.; Kanjanapothi, D.; Tuntiwachwuttikul, P.; Reutrakul, V. Planta Med. 1989, 55, 133 https://doi.org/10.1055/s-2006-961905
  16. Pandji, C.; Grimm, C.; Wray, V.; Witte, L.; Proksch, P. Phytochemistry 1993, 34, 415 https://doi.org/10.1016/0031-9422(93)80020-S
  17. Ungsurungsie, M.; Sutheinkul, D.; Paovalo, C. Food Cosmet. Toxicol. 1982, 120, 527
  18. Murakami, A.; Kondo, A.; Nakamura, Y.; Ohigashi, H.; Koshimizu, K. Biosci. Biotechnol. Biochem. 1993, 57, 1971 https://doi.org/10.1271/bbb.57.1971
  19. The Traditional Medicine Formulations Used in Myanmar Traditional Medicine; Department of Traditional Medicine, Ministry of Health: Myanmar, 1990; p 81
  20. Saralamp, P.; Chuakul, W.; Temsirirkkul, R.; Clayton, T. Medicinal Plants in Thailand; Department of Pharmaceutical Botany, Mahidol University: Bangkok, 1996; Vol 1, p 49
  21. Sawangjaroen, S.; Subhadhirasakul, S.; Phongpaichit, S.; Siripanth, C.; Jamjaroen, K.; Sawangjaroen, K. Parasitol. Res. 2005, 95, 1721
  22. Gu, J.-Q.; Park, E. J.; Vigo, J. S.; Graham, J. G.; Fong, H. H. S.; Pezzuto, J. M.; Kinghorn, A. D. J. Nat. Prod. 2002, 65, 1616 https://doi.org/10.1021/np020249p
  23. Prochaska, H. J.; Santamaria, A. B. Anal. Biochem. 1988, 169, 328 https://doi.org/10.1016/0003-2697(88)90292-8
  24. Zhang, Y.; Talalay, P.; Cho, C. G.; Posner, G. H. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 2399 https://doi.org/10.1073/pnas.89.6.2399
  25. Shibata, K.; Tatsukawa, A.; Umeoka, K.-I.; Lee, H. S.; Ochi, M. Tetrahedron 2000, 56, 8821 https://doi.org/10.1016/S0040-4020(00)00812-7
  26. Lee, Y. R.; Choi, J. H.; Yoon, S. H. Tetrahedron Lett. 2005, 46, 7539 https://doi.org/10.1016/j.tetlet.2005.08.159
  27. Lee, Y. R.; Kim, J. H. Synlett 2007, 2232
  28. Wang, X.; Lee, Y. R. Synthesis 2007, 3044
  29. Wang, X.; Lee, Y. R. Tetrahedron Lett. 2007, 48, 6275 https://doi.org/10.1016/j.tetlet.2007.07.022
  30. Lee, Y. R.; Lee, W. K.; Noh, S. K.; Lyoo, W. S. Synthesis 2006, 853
  31. Lee, Y. R.; Xia, L. Synthesis 2007, 3240
  32. Lee, Y. R.; Kim D. H. Synthesis 2006, 603
  33. Lee, Y. R.; Xia, L. Bull. Korean Chem. Soc. 2007, 28, 1579 https://doi.org/10.5012/bkcs.2007.28.9.1579
  34. Lee, Y. R.; Wang, X.; Kim, Y. M.; Shim, J. J.; Kim, B. N.; Han, D. H. Bull. Korean Chem. Soc. 2007, 28, 1735 https://doi.org/10.5012/bkcs.2007.28.10.1735
  35. Lee, Y. R.; Li, X. Bull. Korean Chem. Soc. 2007, 28, 1739 https://doi.org/10.5012/bkcs.2007.28.10.1739
  36. Lee, Y. R.; Wang, X. Bull. Korean Chem. Soc. 2007, 28, 2061 https://doi.org/10.5012/bkcs.2007.28.11.2061
  37. Lee, Y. R.; Kim, Y. M. Helv. Chim. Acta 2007, 90, 2401 https://doi.org/10.1002/hlca.200790247
  38. Lee, Y. R.; Xia, L. Tetrahedron Lett. 2008, 49, 3283 https://doi.org/10.1016/j.tetlet.2008.03.075
  39. Lee, Y. R.; Li, X.; Kim, J. H. J. Org. Chem. in press
  40. Lee, Y. R.; Xia, L. Synlett. in press

피인용 문헌

  1. Synthetic studies towards the mulberry Diels–Alder adducts: H-bond accelerated cycloadditions of chalcones vol.10, pp.30, 2012, https://doi.org/10.1039/c2ob25115a
  2. Replacement of the Methylene of Dihydrochalcones with Oxygen: Synthesis and Biological Evaluation of 2-Phenoxyacetophenones vol.80, pp.4, 2012, https://doi.org/10.1111/j.1747-0285.2012.01432.x
  3. Renealmia L.f.: aspectos botânicos, ecológicos, farmacológicos e agronômicos vol.17, pp.2, 2015, https://doi.org/10.1590/1983-084X/13_049
  4. Asymmetric Total Synthesis and Biological Evaluation of Proapoptotic Natural Myrcene-Derived Cyclohexenyl Chalcones vol.2018, pp.42, 2018, https://doi.org/10.1002/ejoc.201800262
  5. (X) vol.39, pp.43, 2008, https://doi.org/10.1002/chin.200843207
  6. Biomimetic Dehydrogenative Diels–Alder Cycloadditions: Total Syntheses of Brosimones A and B vol.125, pp.32, 2008, https://doi.org/10.1002/ange.201302847
  7. Biomimetic Dehydrogenative Diels–Alder Cycloadditions: Total Syntheses of Brosimones A and B vol.52, pp.32, 2008, https://doi.org/10.1002/anie.201302847
  8. Chiral Boron Complex-Promoted Asymmetric Diels-Alder Cycloaddition and Its Application in Natural Product Synthesis vol.81, pp.2, 2008, https://doi.org/10.1021/acs.joc.5b02248
  9. Enantioselective Total Syntheses of Kuwanon X, Kuwanon Y, and Kuwanol A vol.18, pp.3, 2016, https://doi.org/10.1021/acs.orglett.5b03285
  10. Total Synthesis of (±)-Kuwanol E vol.79, pp.10, 2016, https://doi.org/10.1021/acs.jnatprod.6b00350
  11. Bioinspired Diastereoconvergent Synthesis of the Tricyclic Core of Palodesangrens via Diels-Alder Reaction, LiAlH4-Mediated Isomerization, and Acid-Mediated Cyclization vol.83, pp.9, 2008, https://doi.org/10.1021/acs.joc.8b00668
  12. The winding road of the uvaretin class of natural products: from total synthesis to bioactive agent discovery vol.10, pp.8, 2008, https://doi.org/10.1039/c9md00052f
  13. Total Synthesis of Palodesangren B Trimethyl Ether and D Dimethyl Ether via a Late-Stage Formation of 2H-Pyran-2-one of the Tetrahydrobenzo[c]pyranochromenone Core vol.84, pp.21, 2008, https://doi.org/10.1021/acs.joc.9b01596
  14. Sterubin: Enantioresolution and Configurational Stability, Enantiomeric Purity in Nature, and Neuroprotective Activity in Vitro and in Vivo vol.26, pp.32, 2008, https://doi.org/10.1002/chem.202001264