PDF herunterladen
Synthesis 2009(8): 1386-1392  
DOI: 10.1055/s-0028-1087993
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Total Syntheses of Leiocarpin A and (-)-Galantinic Acid Starting­ from d-Mannitol

Kommu Nagaiah*, Domalapally Sreenu, Kamaraju V. Purnima, Ramisetti Srinivasa Rao, Jhillu S. Yadav
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: nagaiah@iict.res.in;
Weitere Informationen

Publikationsverlauf

Received 3 December 2008
Publikationsdatum:
06. März 2009 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

Stereoselective total syntheses of leiocarpin A and (-)-galantinic acid, starting from d-mannitol as a chiral synthon, are described. The key steps involve stereoselective allylations, a Grignard reaction to control the required stereogenic centers, and ring-closing metathesis followed by intramolecular Michael addition.

Key words

d-mannitol - allylation - Grignard reaction - ring-closing metathesis - Michael addition

    References and Notes

  • 1a Wu YC. Duh CY. Chang FR. Wang SK. Chang JJ. McPhail DT. Lee KH. J. Nat. Prod.  1991,  54:  1077 
    Google Scholar
  • 1b Sam TW. Saw-Yeu C. Matsjeh S. Gan EK. Razak D. Mohamed AL. Tetrahedron Lett.  1987,  28:  2541 
    Google Scholar
  • 1c Talapatra SK. Basu D. Goaiwami S. Talapatra B. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem.  1985,  24:  29 
    Google Scholar
  • For reviews on the cytotoxic activity and other bioactivity of styryl lactones see:
  • 2a Mereyala HB. Joe M. Curr. Med. Chem. Anti-Cancer Agents  2001,  1:  293 
    Google Scholar
  • 2b Blázquez MA. Bermejo A. Zafra-Polo MC. Cortes D. Phytochem. Anal.  1999,  10:  161 
    Google Scholar
  • 2c Mohd Ridzuan MAR. Ruenruetai U. Noor Rain A. Khozirah S. Zakiah I. Trop. Biomed.  2006,  23:  140 
    Google Scholar
  • 3a Surivet JP. Vatele JM. Tetrahedron Lett.  1998,  39:  7299 
    Google Scholar
  • 3b Prasad KR. Dhaware MG. Synlett.  2007,  1112 
    Google Scholar
  • 3c Mukai C. Hirai S. Hanaoka M. J. Org. Chem.  1997,  62:  6619 
    Google Scholar
  • 3d Dixon DJ. Ley SV. Tate EW. J. Chem. Soc., Perkin Trans. 1  1998,  3125 
    Google Scholar
  • 3e Tate EW. Dixon DJ. Ley SV. Org. Biomol. Chem.  2006,  4:  1698 
    Google Scholar
  • 3f Banwell MG. Coster MJ. Edwards AJ. Karunaratne OP. Smith JA. Welling LL. Willis AC. Aust. J. Chem.  2003,  56:  585 
    Google Scholar
  • 3g Banwell MG. Coster MJ. Karunaratne OP. Smith JA. J. Chem. Soc., Perkin Trans. 1  2002,  1622 
    Google Scholar
  • 3h Ramachandran PV. Chandra JS. Reddy MVR. J. Org. Chem.  2002,  67:  7547 
    Google Scholar
  • 3i Viroleaud MA. Bressy C. Piva O. Tetrahedron Lett.  2003,  44:  8081 
    Google Scholar
  • 3j Nakashima K. Kikuchi N. Shirayama D. Miki T. Ando K. Sono M. Suziki S. Kawase M. Kondoh M. Sato M. Tori M. Bull. Chem. Soc. Jpn.  2007,  80:  387 
    Google Scholar
  • 3k Prasad KR. Dhaware MG. Synlett  2007,  1112 
    Google Scholar
  • 3l Yamshita Y. Saito S. Kobayashi S. J. Am. Chem. Soc.  2003,  125:  3793 
    Google Scholar
  • 3m Chen J. Lin G.-Q. Wang Z.-M. Liu H.-Q. Synlett  2002,  1265 
    Google Scholar
  • 3n Tsubaki M. Kanai K. Nagase H. Honda T. Tetrahedron  1999,  55:  2493 
    Google Scholar
  • 3o Surivet JP. Vatele JM. Tetrahedron  1999,  55:  13011 
    Google Scholar
  • 3p Sabitha G. Sudhakar K. Yadav JS. Synthesis  2007,  385 
    Google Scholar
  • 3q Prasad KR. Gholap SL. Tetrahedron Lett.  2007,  48:  4679 
    Google Scholar
  • 3r Chen J. Lin GQ. Wang ZM. Liu HQ.   , 
  • 4a Mu Q. Tang W. Li C. Lu Y. Sun H. Zheng X. Wu N. Lou B. Xu B. Heterocycles  1999,  12:  2969 
    Google Scholar
  • 4b Mu Q. Li CM. He YN. Sun HD. Zheng HL. Lu Y. Zheng QT. Jiang W. Chin. Chem. Lett.  1999,  10:  135 
    Google Scholar
  • 4c Chen J. Lin GQ. Liu HQ. Tetrahedron Lett.  2004,  45:  8111 
    Google Scholar
  • 5 Shoji j. Sakajaki R. Koizumi K. Mayama M. Matsurra SJ. J. Antibiot.  1975,  28:  122 
    CrossrefGoogle Scholar
  • 6 Sakai N. Ohfune Y. Tetrahedron Lett.  1990,  31:  4151 
    CrossrefGoogle Scholar
  • 7 Sakai N. Ohfune Y. J. Am. Chem. Soc.  1992,  114:  998 
    CrossrefGoogle Scholar
  • 8 Ikota N. Heterocycles  1991,  32:  521 
    CrossrefGoogle Scholar
  • 9 Kumar JSR. Datta A. Tetrahedron Lett.  1999,  40:  1381 
    CrossrefGoogle Scholar
  • 10 Kiyooka S. Goh K. Nakamura Y. Takesue H. Hena MA. Tetrahedron Lett.  2000,  41:  6599 
    CrossrefGoogle Scholar
  • 11 Moreau X. Campagne J. Tetrahedron Lett.  2001,  42:  4467 
    CrossrefGoogle Scholar
  • 12 Raghavan S. Ramakrishna Reddy S. J. Org. Chem.  2003,  68:  5754 
    CrossrefGoogle Scholar
  • 13 Bethuel Y. Gademann K. Synlett  2006,  1580 
    Artikel in Thieme ConnectGoogle Scholar
  • 14 Kumar P. Pandey SK. Kandula SV. Tetrahedron Lett.  2004,  45:  5877 
    CrossrefGoogle Scholar
  • 15a Nagaiah K. Sreenu D. Srinvasa Rao R. Yadav JS. Tetrahedron Lett.  2007,  48:  7173 
    Google Scholar
  • 15b Praveen Kumar S. Nagaiah K. Tetrahedron Lett.  2007,  48:  1391 
    Google Scholar
  • 15c Praveen Kumar S. Nagaiah K. Chorgade MS. Tetrahedron Lett.  2006,  40:  7149 
    Google Scholar
  • 16a Marton D. Stivanello D. Tagliavini G. J. Org. Chem.  1996,  61:  2731 
    Google Scholar
  • 16b Christian P. Jean LL. J. Org. Chem.  1985,  50:  910 
    Google Scholar
  • 16c Molas P. Matheu MI. Castillón S. Tetrahedron Lett.  2004,  45:  3721 
    Google Scholar
  • 16d Miranda LSM. Meireles BA. Costa JS. Pereira VLP. Vasconcellos MLAA. Synlett  2005,  869 
    Google Scholar
  • 16e Paterson I. Anderson EA. Dalby SM. Genovino J. Lim JH. Moessner C. Chem. Commun.  2007,  1852 
    Google Scholar
  • 16f Radha Krishna P. Ramana Reddy VV. Srinivas R. Tetrahedron  2007,  63:  9871 
    Google Scholar
  • 17a Yong X. Glenn DP. J. Org. Chem.  2002,  67:  7158 
    Google Scholar
  • 17b Jackson DY. Synth. Commun.  1988,  18:  337 
    Google Scholar
  • 17c Janusz J. Stanislaw P. Tomasz B. Tetrahedron  1986,  42:  447 
    Google Scholar
  • 18 Rodriguez A. Nomen M. Spur BW. Godfroid JJ. Tetrahedron Lett.  1999,  40:  5161 
    CrossrefGoogle Scholar
  • 19 Rama Rao AV. Mysorekar SV. Gurjar MK. Yadav JS. Tetrahedron Lett.  1987,  28:  2183 
    CrossrefGoogle Scholar
  • 20 Quinn KJ. Smith AG. Cammrano CM. Tetrahedron  2007,  63:  4881 
    CrossrefGoogle Scholar
  • 21 Prashad M. Kim HY. Lu Y. Liu Y. Har D. Repic O. Blacklock TJ. Giannousis P. J. Org. Chem.  1999,  64:  1750 
    CrossrefGoogle Scholar
  • For the use of magnesium bromide diethyl etherate in the allylstannane reaction, see:
  • 22a Lee E. Jeong EJ. Kang EJ. Sung LT. Hong SK. J. Am. Chem. Soc.  2001,  123:  10131 
    Google Scholar
  • 22b Keck GE. Abbott DE. Tetrahedron Lett.  1984,  25:  1883 
    Google Scholar