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Synthesis 2010(20): 3493-3503  
DOI: 10.1055/s-0030-1258226
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Hanagokenol A, (+)-Fortunins E, G, H, and (-)-Sugikurojin A from Abietic Acid

Enrique Alvarez-Manzaneda*a, Rachid Chahbouna, Esteban Alvareza, Jose M. Ramosa, Juan J. Guardiaa, Ibtissam Messouria, Ikram Chaybouna, Ahmed I. Mansourb, Abdelaziz Dahdouhb
a Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain
Fax: +34(958)248089; e-Mail: eamr@ugr.es;
b Laboratoire de Chimie Organique Appliquée, Département de Chimie, Faculté des Sciences, Université Abdelmalek Essaâdi, Tetouan, Morocco
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Publication History

Received 28 May 2010
Publication Date:
20 August 2010 (online)

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Abstract

A series of 12-hydroxy-substituted abietane diterpenes, functionalized on C19 or C18, have been synthesized starting from 18-hydroxyferruginol. The first synthesis of antibacterial hanagokenol A and fortunins E, G, and H, and a new procedure for preparing sugikurojin A and the immunosuppressive 19-hydroxy­-ferruginol are reported.

Key words

antibiotics - diastereoselectivity - phenols - terpenoids - oxidation

    References

  • 1a Kupchan SM. Karim A. Marcks C. J. Org. Chem.  1969,  34:  3912 
    Google Scholar
  • 1b Kupchan SM. Karim A. Marcks C. J. Am. Chem. Soc.  1968,  90:  5923 
    Google Scholar
  • 2a Gil RR. Cordell GA. J. Nat. Prod.  1994,  57:  181 
    Google Scholar
  • 2b Lin LZ. Blasko G. Cordell GA. Phytochemistry  1989,  28:  177 
    Google Scholar
  • 3 Son K.-H. Oh H.-M. Choi S.-K. Han D.-C. Kwon B.-M. Bioorg. Med. Chem. Lett.  2005,  15:  2019 
    CrossrefGoogle Scholar
  • 4 Campello J. de P.. Fonseca SF. Cnag C.-J. Wenkert E. Phytochemistry  1975,  14:  243 
    CrossrefGoogle Scholar
  • 5 Machida K. Shioda K. Yapita Y. Kakuda R. Kikuchi M. Nat. Med.  2001,  55:  147 
    Google Scholar
  • 6 Arihara S. Umeyama A. Bando S. Imoto S. Ono M. Tani M. Yoshikawa K. Chem. Pharm. Bull.  2004,  52:  354 
    CrossrefPubMedGoogle Scholar
  • 7 Cambie RC. Cox RE. Sidwell D. Phytochemistry  1984,  23:  333 
    CrossrefGoogle Scholar
  • 8 Takei M. Umeyama A. Arihara S. Biochem. Biophys. Res. Commun.  2005,  337:  730 
    CrossrefPubMedGoogle Scholar
  • 9 Kinouchi Y. Ohtsu H. Tokuda H. Nishino H. Matsunaga S. Tanaka R. J. Nat. Prod.  2000,  63:  817 
    CrossrefGoogle Scholar
  • 10a Fukushima I. Sayama Y. Kyogoku K. Murayama H. Agric. Biol. Chem.  1968,  32:  1103 
    Google Scholar
  • 10b Harrison LJ. Asakawa Y. Phytochemistry  1987,  26:  1211 
    Google Scholar
  • 11 Yoshikawa K. Kokudo N. Tanaka M. Nakano T. Shibata H. Haragaki N. Higuchi T. Hashimoto T. Chem. Pharm. Bull.  2008,  56:  89 
    CrossrefGoogle Scholar
  • 12 Yao S. Tang C.-P. Ke C.-Q. Ye Y. J. Nat. Prod.  2008,  71:  1242 
    CrossrefGoogle Scholar
  • 13 Harring SR. Livinghouse T. Tetrahedron Lett.  1989,  30:  1499 
    CrossrefGoogle Scholar
  • 14a Engler TA. Sampath U. Naganathan S. Vander Velde D. Takusagawa F. J. Org. Chem.  1989,  54:  5712 
    Google Scholar
  • 14b Zambrano JL. Rosales V. Nakano T. Tetrahedron Lett.  2003,  44:  1859 
    Google Scholar
  • 15a Banik BK. Ghosh S. Ghatak VR. Tetrahedron  1988,  44:  6947 
    Google Scholar
  • 15b Majetich G. Siesel D. Synlett  1995,  559 
    Google Scholar
  • 15c Majetich G. Liu S. Fang J. Siesel D. Zhang Y. J. Org. Chem.  1997,  62:  6928 
    Google Scholar
  • 15d Tada M. Nishiiri S. Zhixiang Y. Imai Y. Tajima S. Okazaki N. Kitano Y. Chiba K. J. Chem. Soc., Perkin Trans. 1  2000,  2657 
    Google Scholar
  • 16 Shishido K. Got K. Miyoshi S. Takaishi Y. Shibuya M. J. Org. Chem.  1994,  59:  406 
    CrossrefGoogle Scholar
  • 17 Bhar SS. Ramana MMV. J. Org. Chem.  2004,  69:  8935 
    CrossrefGoogle Scholar
  • 18a Huffman JW. J. Org. Chem.  1970,  35:  3154 
    Google Scholar
  • 18b Banerjee AK. Acevedo JC. Canudes-Gonzalez N. Bull. Soc. Chim. Belg.  1990,  99:  9 
    Google Scholar
  • 18c Cambie RC. Rutledge PS. Woodgate PD. Aust. J. Chem.  1993,  46:  1447 
    Google Scholar
  • 18d Burnell RH. Cote C. Girard M. J. Nat. Prod.  1993,  56:  461 
    Google Scholar
  • 19 Haslinger E. Michl G. Tetrahedron Lett.  1988,  29:  5754 
    Google Scholar
  • 20 Takemura S. Matsubara Y. Obata T. Zhou Z. Fujiwara Y. Nippon Kagaku Kaishi  1994,  545 
    Google Scholar
  • 21a Cambie RC. Franich RA. Aust. J. Chem.  1971,  24:  134 
    Google Scholar
  • 21b Akita H. Oishi T. Chem. Pharm. Bull.  1981,  29:  1579 
    Google Scholar
  • 22 Alvarez-Manzaneda E. Chaboun R. Cabrera E. Alvarez E. Alvarez-Manzaneda R. Lachkar M. Messouri I. Tetrahedron Lett.  2007,  48:  989 
    CrossrefGoogle Scholar
  • 23 Carman RM. Deeth HC. Marti RA. Mori K. Matsui M. Tetrahedron Lett.  1968,  9:  3359 
    CrossrefGoogle Scholar
  • 24 Alvarez-Manzaneda E. Chahboun R. Cabrera E. Alvarez E. Alvarez-Manzaneda R. Lachkar M. Messouri I. Synlett  2007,  2425 
    Article in Thieme ConnectGoogle Scholar
  • 25 Pelletier SW. Herald DL. J. Chem. Soc., Chem. Commun.  1971,  10 
    Google Scholar
  • 26 Tagat JR. Nazareno DV. Puar MS. McCombie SW. Ganguly AK. Bioorg. Med. Chem. Lett.  1994,  4:  1101 ; and references cited therein
    CrossrefGoogle Scholar
  • 27 Barrero AF. Alvarez-Manzaneda E. Alvarez-Manzaneda R. Chahboun R. Meneses R. Aparicio MB. Synlett  1999,  713 
    Article in Thieme ConnectGoogle Scholar