Synthesis 2011(23): 3807-3814  
DOI: 10.1055/s-0031-1289293
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Synthesis of Novel Jolkinolides and Related Derivatives Starting from Stevioside

Lian-Yong Shia, Jia-Qiang Wua, Da-Yong Zhang*a, Yang-Chang Wub, Wei-Yi Huaa, Xiao-Ming Wu*a
a Center of Drug Discovery, College of Pharmacy, China Pharmaceutical University, 24 Tongjia Xiang Road, Nanjing 210009, P. R. of China
Fax: +86(25)83271307; e-Mail: zhangdayong@cpu.edu.cn; e-Mail: xmwu@cpu.edu.cn;
b Graduate Institute of Pharmaceutical Chemistry, College of Pharmacy, China Medical University, 91 Hsueh-Shih Road, Taichung 40402, Taiwan
Weitere Informationen

Publikationsverlauf

Received 11 July 2011
Publikationsdatum:
20. Oktober 2011 (online)

Abstract

Jolkinolides are naturally occurring tetracyclic diterpene from Euphorbia genus, which exhibit promising antitumor and other biological activity. Efficient syntheses of the 19-carboxy derivative of jolkinolide A and 19-hydroxyjolkinolide E have been accomplished in 13 steps with a total yield of 7.8% starting from the easily available and low-cost sweetener stevioside, and some related derivatives have also been synthesized.

    References and Notes

  • 1a Che C.-T. Zhou T.-X. Ma Q.-G. Qin G.-W. Williams I.-D. Wu H.-M. Shi Z.-S. Phytochemistry  1999,  52:  117 
  • 1b Sutthivaiyakit S. Thapsut M. Prachayasittikul V. Phytochemistry  2000,  53:  947 
  • 1c Wang Y.-B. Huang R. Wang H.-B. Jin H.-Z. Lou L.-G. Qin G.-W. J. Nat. Prod.  2006,  69:  967 
  • 2a Shi YP. He ZJ. Jia JZ. Nat. Prod. Res. Dev.  1999,  11:  85 
  • 2b Su X.-L. Lin R.-C. Wong S.-K. Tsui S.-K. Kwan S.-Y. Phytochem. Anal.  2003,  14:  40 
  • 3a Zhang DY. Shi LY. Wu XM. Chin. J. Org. Chem.  2009,  29:  188 
  • 3b Lai AR. Cambie RC. Rutledge PS. Woogate PD. Phytochemistry  1990,  29:  2239 
  • 3c Luo H.-Y. Wang A.-Q. Can. J. Physiol. Pharmacol.  2006,  84:  959 
  • 3d Yamaguchi K. Uemura D. Tsuji T. Kondo K. Biosci. Biotechnol. Biochem.  1994,  58:  1749 
  • 4 Shi H.-M. Williams ID. Sung HY. Zhu H.-X. Ip NY. Min Z.-D. Planta Med.  2005,  71:  349 
  • 5a Yan S.-S. Li Y. Wang Y. Shen S.-S. Gu Y. Wang H.-B. Qin G.-W. Yu Q. Mol. Cancer Ther.  2008,  7:  1523 
  • 5b Wang Y. Ma X. Yan S. Shen S. Zhu H. Gu Y. Wang H. Qin G. Yu Q. Cancer. Res.  2009,  69:  7302 
  • 6 Katsumura S. Kimura A. Isoe S. Tetrahedron  1989,  45:  1337 
  • 7 Ogawa T. Nozaki M. Matsui M. Tetrahedron  1980,  36:  2641 
  • 8a Cui Y.-M. Yasutomi E. Otani Y. Yoshinaga T. Ido K. Sawada K. Ohwada T. Bioorg. Med. Chem. Lett.  2008,  18:  5197 
  • 8b Singh SB. Ondeyka JG. Liu W. Chen S. Chen TS. Li X. Bouffard A. Dropinski J. Jones AB. McCormick S. Hayes N. Wang J. Sharma N. MacNaul K. Hernandez M. Chao Y.-S. Baffic J. Lam M.-H. Burton C. Sparrow CP. Menke JG. Bioorg. Med. Chem. Lett.  2005,  15:  2824 
  • 9 Blay G. Garcia B. Molina E. Pedro JR. Tetrahedron  2007,  63:  9621 
  • 10 Terai T. Ren H. Mori G. Yashihito Y. Hayashi T. Chem. Pharm. Bull.  2002,  50:  1007 
  • 11 Bailey PS. Chem. Rev.  1958,  58:  925 
  • 12a McMurry JE. Blaszczak LC. J. Org. Chem.  1974,  39:  2217 
  • 12b Schultz AG. Wang A. J. Org. Chem.  1996,  61:  4857 
  • 13 Wasserman HH. Ives JL. J. Am. Chem. Soc.  1976,  98:  7868 
  • 14a Jiang B. Shi H.-P. Tian W.-S. Zhou W.-S. Tetrahedron  2008,  64:  469 
  • 14b Furber M. Mander LN. Patrick GL. J. Org. Chem.  1990,  55:  4860 
  • 15a Rubottom GM. Vazquez MA. Pelegrina DR. Tetrahedron Lett.  1974,  15:  4319 
  • 15b Rubottom GM. Gruber JM. Boeckman RK. Ramaiah M. Medwid JB. Tetrahedron Lett.  1978,  19:  4603 
  • 16 Mosettig E. Beglinger U. Dolder F. Lichti H. Quitt P. Waters JA. J. Am. Chem. Soc.  1963,  85:  2305 
  • 17 Miyake T. Kigoshi H. Akita H. Tetrahedron: Asymmetry  2007,  18:  2915 
  • 18 Lai G.-F. Wang X.-Y. Wang Y.-F. Cao J.-X. Luo S.-D. Ju P. Helv. Chim. Acta  2009,  92:  470