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Synthesis 2012(4): 585-590  
DOI: 10.1055/s-0031-1290156
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Total Synthesis of Putaminoxin

Jhillu Singh Yadav*a,b, Ande Rajua,c, Kontham Ravindara, Basi V. Subba Reddya, Ahmad Al Khazim Al Ghamdib
a Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 607, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
b Engineer Abdullah Baqshan for Bee Research, King Saudi University, Saudi Arabia
c University of Hyderabad, Hyderabad 500046, India
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Publication History

Received 14 October 2011
Publication Date:
16 January 2012 (online)

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Abstract

The stereoselective total synthesis of a phytotoxic macrolide putaminoxin, isolated from the culture of Phoma putaminum fungus, has been accomplished by utilization of Sharpless asymmetric epoxidation, Birch reduction, Jacobsen’s kinetic resolution of racemic epoxide, and Yamaguchi lactonization as key transformations.

Key words

macrolide - necrotic leaf disease - Sharpless asymmetric epoxidation - Birch reduction - Jacobsen’s kinetic resolution - Yamaguchi lactonization

    References

  • 1 Evidente A. Lanzetta R. Capasso R. Andolfi A. Bottalico A. Vurro M. Zonno MC. Phytochemistry  1995,  40:  1637 
    Google Scholar
  • 2 Fuschser J. Zeeck A. Liebigs Ann./Recl.  1997,  87 
    Google Scholar
  • 3 Sabitha G. Padmaja P. Reddy PN. Yadav JS. Tetrahedron Lett.  2010,  51:  6166 
    Google Scholar
  • 4 Evidente A. Capasso R. Andolfi A. Vurro M. Zonno MC. Nat. Toxins  1998,  6:  183 
    Google Scholar
  • 5a Sabitha G. Yadagiri K. Swapna R. Yadav JS. Tetrahedron Lett.  2009,  50:  5417 
    Google Scholar
  • 5b Kamal A. Reddy PV. Balakrishna M. Prabhakar S. Lett. Org. Chem.  2011,  8:  143 
    Google Scholar
  • 6 Smith AB. Lin Q. Doughty VA. Zhuang L. McBriar MD. Kerns JK. Boldi AM. Murase N. Moser WH. Brook CS. Bennett CS. Nakayama K. Sobukawa M. Lee Trout RE. Tetrahedron  2009,  65:  6470 
    Google Scholar
  • 7a Osterkamp F. Ziemer B. Koert U. Wiesner M. Raddatz P. Goodman SL. Chem. Eur. J.  2000,  6:  666 
    Google Scholar
  • 7b Pihko PM. Aho JE. Org. Lett.  2004,  6:  3849 
    Google Scholar
  • 8 Liu J. Yang JH. Ko C. Hsung RP. Tetrahedron Lett.  2006,  47:  6121 
    Google Scholar
  • 9a Yadav JS. Sreenivas M. Reddy AS. Reddy BVS. J. Org. Chem.  2010,  75:  8307 
    Google Scholar
  • 9b Perepogu AK. Raman D. Murty USN. Rao VJ. Bioorg. Chem.  2009,  37:  46 
    Google Scholar
  • 10a Finn MG. Sharpless KB. In Asymmetric Synthesis   Vol. 5:  Morrison JD. Acadamic Press; New York: 1985.  Chap. 8. p.247 
    Google Scholar
  • 10b Pfenninger A. Synthesis  1986,  89 
    Google Scholar
  • 10c Katsuki T. Sharpless KB. J. Am. Chem. Soc.  1980,  102:  5974 
    Google Scholar
  • 10d Gao Y. Hanson RM. Klunder JM. Ko SY. Masamune H. Sharpless KB. J. Am. Chem. Soc.  1987,  109:  5765 
    Google Scholar
  • 10e Yadav JS. Reddy ChS. Org. Lett.  2009,  11:  1705 
    Google Scholar
  • 11 Yadav JS. Deshpande PK. Sharma GVM. Tetrahedron  1990,  46:  7033 
    Google Scholar
  • 12a Braun MG. Vincent A. Boumediene M. Prunet J. J. Org. Chem.  2011,  76:  4921 
    Google Scholar
  • 12b Florence GJ. Cadou RF. Tetrahedron Lett.  2010,  51:  5761 
    Google Scholar
  • 12c Tokunaga M. Larrow JF. Kakiuchi F. Jacobsen EN. Science  1997,  277:  936 
    Google Scholar
  • 12d Kretschmer M. Menche D. Synlett  2010,  2989 
    Google Scholar
  • 13a Van de Weghe P. Bourg S. Eustache S. Tetrahedron  2003,  59:  7365 
    Google Scholar
  • 13b Burova SA. McDonald FE. J. Am. Chem. Soc.  2002,  124:  8188 
    Google Scholar
  • 13c Yadav JS. Sipak J. Dutta SK. Kunwar AC. Tetrahedron Lett.  2007,  48:  5335 
    Google Scholar
  • 14 Naidu VS. Gupta P. Kumar P. Tetrahedron  2007,  63:  7624 
    Google Scholar
  • 15a Hansen MT. Florence GJ. Lugo-Mas P. Chen J. Abrams JC. Forsyth CJ. Tetrahedron Lett.  2003,  44:  57 
    Google Scholar
  • 15b Bal BS. Childers WE. Pinnick HW. Tetrahedron  1981,  37:  2091 
    Google Scholar
  • 15c Yadav JS. Thrimurthulu N. Venkatesh M. Rao KVR. Prasad AR. Reddy BVS. Synthesis  2010,  73 
    Google Scholar
  • 16a Shiina I. Fujisawa H. Ishii T. Fukuda Y. Heterocycles  2000,  52:  1105 
    Google Scholar
  • 16b Sabitha G. Reddy RT. Ramesh M. Srinivas C. Yadav JS. Bull. Chem. Soc. Jpn.  2011,  84:  229 
    Google Scholar
  • 16c Kaliappan KP. Si D. Synlett  2009,  2441 
    Google Scholar
  • 17 Srihari P. Kumaraswamy B. Somaiah K. Yadav JS. Synthesis  2010,  1039 
    Google Scholar