Transition-Metal-Catalyzed Regio- and Diastereoselective 1,4-Conjugate Addition­ of Zerumbone Using Boronic Acids: A Simple Route toward Novel Zerumbone Derivatives

Abstract

A straightforward method for the synthesis of novel derivatives­ of zerumbone via palladium- and rhodium-catalyzed regio­- and diastereoselective 1,4-conjugate addition using boronic acids is developed. The reaction is general for aryl boronic acids containing both electron-donating and electron-withdrawing groups.

Key words

zerumbone - rhodium - palladium - 1,4-conjugate addition - boronic acids

• References

• 1a Chin Y.-W, Balunas MJ, Chai H.-B, Kinghorn AD. AAPS J. 2006; 8: E239
• 1b Itokawa H, Morris-Natschke SL, Akiyama T, Lee KH. J. Nat. Med. 2008; 62: 263
• 2 Strohl WR. Drug Discovery Today 2000; 5: 39
• 3 Newman DJ, Cragg GM. J. Nat. Prod. 2007; 70: 461
• 4a Dev S. Tetrahedron 1960; 8: 171
• 4b Damodaran NP, Dev S. Tetrahedron Lett. 1965; 1977
• 4c Dev S, Anderson JE, Cormier V, Damodaran NP, Roberts JD. J. Am. Chem. Soc. 1968; 90: 1246
• 4d Hall SR, Nimgirawath S, Raston CL, Sittatrakkul A, Thadaniti S, Thirasasana N, White AH. Aust. J. Chem. 1981; 34: 2243
• 4e Fransworth NR, Bunyapraphatsara N. Thai Medical Plants . Prachachon; Bangkok: 1992: 261
• 4f Sawada S, Yokoi T, Kitayama T. Aroma Res. 2002; 9: 34; and references cited therein
• 5a Murakami A, Tanaka T, Lee JY, Surh YJ, Kim HW, Kawabata K, Nakamura Y, Jiwajinda S, Ohigashi H. Int. J. Cancer 2004; 110: 481
• 5b Kirana C, McIntosh GH, Record IR, Jones GP. Nutr. Cancer 2003; 45: 218
• 6a Ozaki Y, Kawahara N, Harada M. Chem. Pharm. Bull. 1991; 39: 2353
• 6b Sulaiman MR, Perimal EK, Akhtar MN, Mohamad AS, Khalid MH, Tasrip NA, Mokhtar F, Zakaria ZA, Lajis NH, Israf DA. Fitoterapia 2010; 81: 855
• 6c Szabolcs A, Tiszlavicz L, Kaszaki J, Pósa A, Berkó A, Varga IS, Boros I, Szüts V, Lonovics J, Takács T. Pancreas 2007; 35: 249
• 6d Murakami A, Ohigashi H. Int. J. Cancer 2007; 121: 2357
• 6e Murakami A, Miyamoto M, Ohigashi H. Biofactors 2004; 21: 95
• 7a Aggarwal BB, Ajaikumar BK, Harikumar KB, Sheeja TT, Sung B, Anand P. Planta Med. 2008; 74: 1560; and references cited therein
• 7b Taha MM, Abdul AB, Abdullah R, Ibrahim TA, Abdelwahab SI, Mohan S. Chem. Biol. Interact. 2010; 186: 295
• 7c Abdelwahab SI, Abdul AB, Mohan S, Taha MM, Syam S, Ibrahim MY, Mariod AA. Leukemia Res. 2011; 35: 268
• 7d Sung B, Prasad S, Yadav VR, Aggarwal BB. Nutr. Cancer. 2012; 64: 173
• 7e Abdelwahab SI, Abdul AB, Zain ZN, Hadi AH. A. Int. Immunopharmacol. 2012; 12: 594
• 8 Dai JR, Cardellina JH, McMahon JB, Boyd MR. Nat. Prod. Lett. 1997; 10: 115
• 9a Kitayama T, Yamamoto K, Utsumi R, Takatani M, Hill RK, Kawai Y, Sawada S, Okamoto T. Biosci. Biotechnol. Biochem. 2001; 65: 2193
• 9b Kitayama T, Iwabuchi R, Minagawa S, Shiomi F, Cappiello J, Sawada S, Utsumi R, Okamoto T. Bioorg. Med. Chem. Lett. 2004; 14: 5943
• 9c Kitayama T, Iwabuchi R, Minagawa S, Sawada S, Okumura R, Hoshino K, Cappiello J, Utsumi R. Bioorg. Med. Chem. Lett. 2007; 17: 1098
• 9d Ohinishi K, Irie K, Murakami A. Biosci. Biotechnol. Biochem. 2009; 73: 1905
• 9e Songsiang U, Pitchuanchom S, Boonyarat C, Hahnvajanawong C, Yenjai C. Eur. J. Med. Chem. 2010; 45: 3794
• 10 Baby S, Dan M, Thaha AR. M, Johnson AJ, Kurup R, Balakrishnapillai P, Lim CK. Flavour Fragr. J. 2009; 24: 301
• 11 Kitayama T. Biosci. Biotechnol. Biochem. 2011; 75: 199; and references cited therein
• 12a Kitayama T, Okamoto T, Hill RK, Kawai Y, Takahashi S, Yonemori S, Yamamoto Y, Ohe K, Uemura S, Sawada S. J. Org. Chem. 1999; 64: 2667
• 12b Ohe K, Miki K, Yanagi S, Tanaka T, Sawada S, Uemura S. J. Chem. Soc., Perkin Trans. 1 2000; 3627
• 13 Kitayama T, Yokoi T, Kawai Y, Hill RK, Morita M, Okamoto T, Yamamoto Y, Fokin VV, Sharpless KB, Sawada S. Tetrahedron 2003; 59: 4857
• 14 Kitayama T, Masuda T, Sakai K, Imada C, Yonekura Y, Kawai Y. Tetrahedron 2006; 62: 10859
• 15a Kitayama T, Masuda T, Kawai Y, Hill RK, Takatani M, Sawada S, Okamoto T. Tetrahedron: Asymmetry 2001; 12: 2805
• 15b Kitayama T, Furuya A, Moriyama C, Masuda T, Fushimi S, Yonekura Y, Kubo H, Kawai Y, Sawada S. Tetrahedron: Asymmetry 2006; 17: 2311
• 16a Sakai M, Hayashi H, Miyaura N. Organometallics 1997; 16: 4229
• 16b Takaya Y, Ogasawara M, Hayashi T, Sakai M, Miyaura N. J. Am. Chem. Soc. 1998; 120: 5579
• 16c Hayashi T. Synlett 2001; 879
• 16d Ramnauth J, Poulin O, Bratovanov SS, Rakhit S, Maddaford SP. Org. Lett. 2001; 3: 2571
• 16e Hayashi T, Takahashi M, Takaya Y, Ogasawara M. J. Am. Chem. Soc. 2002; 124: 5052
• 16f Hayashi T, Yamasaki K. Chem. Rev. 2003; 103: 2829
• 16g Navarre L, Pucheault M, Darses S, Genet JP. Tetrahedron Lett. 2005; 46: 4247
• 16h Edwards HJ, Hargrave JD, Penrose SD, Frost CG. Chem. Soc. Rev. 2010; 39: 2093
• 16i Zilaout H, van den Hoogenband A, de Vries J, Lange JH. M, Terpstra JW. Tetrahedron Lett. 2011; 52: 5934
• 17a Chen L, Li CJ. Chem. Commun. 2004; 2362
• 17b Lu X, Lin S. J. Org. Chem. 2005; 70: 9651
• 17c Gini F, Hessen B, Minnaard AJ. Org. Lett. 2005; 7: 5309
• 17d Yamamoto T, Iizuka M, Ohta T, Ito Y. Chem. Lett. 2006; 35: 198
• 17e Gini F, Hessen B, Feringa BL, Minnaard AJ. Chem. Commun. 2007; 710
• 18 See the experimental section.
• 19 Compound 3a was recrystallized from EtOAc–hexane to give crystals which were suitable for single crystal X-ray analysis (CCDC 910243). Unit cell parameters: a = 11.3478(5) Å, b = 12.8754(6) Å, c = 12.5373(6) Å, β = 95.178(2)°, space group = P2₁.