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Synthesis 2010(14): 2407-2412  
DOI: 10.1055/s-0029-1218775
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Stereoselective Aldol Approach for the Total Synthesis of Herbarumin I and Stagonolide A

P. Srihari*, G. Maheswara Rao, R. Srinivasa Rao, J. S. Yadav
Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad 500607, India
Fax: +91(40)27160512; Fax: +91(40)27160387; e-Mail: srihari@iict.res.in;
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Publication History

Received 8 March 2010
Publication Date:
05 May 2010 (online)

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Abstract

A stereoselective total synthesis of phytotoxic compounds herbarumin I and stagonolide A has been achieved utilizing Crimmin’s protocol for non-Evans anti-aldol approach and a ring-closing olefin metathesis reaction as the key steps.

Key words

macrolide - phytotoxic - Evans aldol - olefin metathesis

    References

  • 1a Dräger G. Kirschning A. Thiericke R. Zerlin M. Nat. Prod. Rep.  1996,  365 
    Google Scholar
  • 1b Riatto VB. Pilli RA. Victor MM. Tetrahedron  2008,  64:  2279 
    Google Scholar
  • 1c Boonphong S. Kittakoop P. Isaka M. Pittayakhajonwut D. Tankicharoen M. Thebtaranonth Y. J. Nat. Prod.  2001,  64:  965 
    Google Scholar
  • 1d Ishigami K. Biosci. Biotechnol. Biochem.  2009,  73:  971 
    Google Scholar
  • 1e Greve H. Schupp PJ. Eguereva E. Kehraus S. König GM. J. Nat. Prod.  2008,  71:  1651 
    Google Scholar
  • 2a Rivero-Cruz JF. Garcia-Aguieee G. Cerda-Garcia-Rojas CM. Mata R. Tetrahedron  2000,  56:  5337 
    Google Scholar
  • 2b Rivero-Cruz JF. Martha M. Cerda-Garcia-Rojas CM. Mata R. J. Nat. Prod.  2003,  66:  511 
    Google Scholar
  • For isolation of stagonolides:
  • 3a Yuzikhin O. Mitina G. Berestetskiy A. J. Agric. Food Chem.  2007,  55:  7707 
    Google Scholar
  • 3b Evidente A. Cimmino A. Berestetskiy A. Mitina G. Andolfi A. Motta . J. Nat. Prod.  2008,  71:  31 
    Google Scholar
  • 3c Evidente A. Cimmino A. Berestetskiy A. Andolfi A. Motta A. J. Nat. Prod.  2008,  71:  1897 
    Google Scholar
  • 4 Tsuda M. Mugishima T. Komatsu K. Sone T. Tanaka M. Mikami Y. Kobayashi J. J. Nat. Prod.  2003,  66:  412 
    CrossrefPubMedGoogle Scholar
  • For syntheses of herbarumin I, see:
  • 5a Furstner A. Radkowski K. Chem. Commun.  2001,  671 
    Google Scholar
  • 5b Furstner A. Radkowski K. Wirtz C. Goddard R. Lehmann WC. Mynott R. J. Am. Chem. Soc.  2002,  124:  7061 
    Google Scholar
  • 5c Sabino AA. Pilli RA. Tetrahedron Lett.  2002,  43:  2819 
    Google Scholar
  • 5d Nagaiah K. Sreenu D. Rao RS. Yadav JS. Tetrahedron Lett.  2007,  48:  7173 
    Google Scholar
  • 5e Selvam PJJ. Rajesh K. Suresh V. Chanti BD. Venkateshwarlu Y. Tetrahedron: Asymmetry  2009,  20:  1115 
    Google Scholar
  • 5f Kamal A. VenkataReddy P. Prabhakar S. Tetrahedron: Asymmetry  2009,  20:  1120 
    Google Scholar
  • 5g Srihari P. Kumaraswamy B. Maheswara Rao G. Yadav JS. Tetrahedron: Asymmetry  2010,  21:  106 
    Google Scholar
  • For syntheses of herbarumin II, see:
  • 6a Diez E. Dixon DJ. Ley SV. Polara A. Rodriguez F. Helv. Chim. Acta  2003,  86:  3717 
    Google Scholar
  • 6b Diez E. Dixon DJ. Ley SV. Polara A. Rodriguez F. Synlett  2003,  1186 
    Google Scholar
  • For syntheses of herbarumin III, see:
  • 7a Gurjar MK. Karmakar S. Mohapatra DK. Tetrahedron Lett.  2004,  45:  4525 
    Google Scholar
  • 7b Nanda S. Tetrahedron Lett.  2005,  46:  3661 
    Google Scholar
  • 7c Salaskar A. Sharma A. Chattopadhyay S. Tetrahedron: Asymmetry  2006,  17:  325 
    Google Scholar
  • 7d Gurjar MK. Nagaprasad R. Ramana CV. Karmakar S. Mohapatra DK. ARKIVOC  2005,  (iii):  237 
    Google Scholar
  • 7e Boruwa J. Gogoi N. Barua NC. Org. Biomol. Chem.  2006,  4:  3521 
    Google Scholar
  • 7f Chen XS. Da S J. Xu B.-Y. Xie Z.-X. Li Y. Chem. J. Chin. Univ.  2007,  28:  2086 
    Google Scholar
  • 7g Chen XS. Da S J. Yang LH. Xu BY. Xie ZX. Li Y. Chin. Chem. Lett.  2007,  18:  255 
    Google Scholar
  • 7h Gupta P. Kumar P. Tetrahedron: Asymmetry  2007,  18:  1688 
    Google Scholar
  • 7i Lee J. Jung YH. Tae J. Bull. Korean Chem. Soc.  2007,  28:  513 
    Google Scholar
  • 7j Mohapatra DK. Ramesh DK. Giardello MA. Chorghade MS. Gurjar MK. Grubbs RH. Tetrahedron Lett.  2007,  48:  2621 
    Google Scholar
  • 7k Yadav JS. Kumar VN. Rao RS. Srihari P. Synthesis  2008,  1938 
    Google Scholar
  • For syntheses of stagonolides see
  • 8a Perepogu AK. Raman D. Murty USN. Rao VJ. Bioorg. Chem.  2009,  37:  46 
    Google Scholar
  • 8b Jana N. Mahapatra T. Nanda S. Tetrahedron: Asymmetry  2009,  20:  2622 
    Google Scholar
  • 8c Giri AG. Mohabul A. Mondal MA. Vedava Puranik VG. Ramana CV. Org. Biomol. Chem.  2010,  8:  398 
    Google Scholar
  • 8d Srihari P. Kumaraswamy B. Somaiah R. Yadav JS. Synthesis  2010,  1039 
    Google Scholar
  • For syntheses of modiolides, see:
  • 9a Mohapatra DK. Dash U. Naidu PR. Synlett  2009,  2129 
    Google Scholar
  • 9b Matsuda M. Yamazaki T. Fuhshuku K. Sugai T. Tetrahedron  2007,  63:  8752 
    Google Scholar
  • For our few recent contributions on smaller than 10-membered-ring lactones, see:
  • 10a Yadav JS. Rajendar G. Ganganna B. Srihari P. Tetrahedron Lett.  2010,  51:  2154 
    Google Scholar
  • 10b Srihari P. Vijaya Bhasker E. Bal Reddy A. Yadav JS. Tetrahedron Lett.  2009,  50:  2420 
    Google Scholar
  • 10c Srihari P. Rajendar G. Srinivasa Rao R. Yadav JS. Tetrahedron Lett.  2008,  49:  5590 
    Google Scholar
  • 10d Srihari P. Kumar BP. Subbarayudu K. Yadav JS. Tetrahedron Lett.  2007,  48:  6977 
    Google Scholar
  • 10e Srihari P. Bhasker EV. Harshavardhan SJ. Yadav JS. Synthesis  2006,  4041 
    Google Scholar
  • 10f Srihari P. Ravindar K. Somaiah R. Yadav JS. Synth. Commun.  2008,  38:  1389 
    Google Scholar
  • For larger than 10-membered ring lactones, see:
  • 10g Srihari P. Kumaraswamy B. Yadav JS. Tetrahedron  2009,  65:  6304 
    Google Scholar
  • 10h Yadav JS. Srihari P. Tetrahedron: Asymmetry  2004,  15:  81 
    Google Scholar
  • 11 Crimmins MT. Mcdougall PJ. Org. Lett.  2003,  5:  591 
    CrossrefPubMedGoogle Scholar
  • 12 Mulzer J. Angermann A. Tetrahedron Lett.  1983,  24:  2843 
    CrossrefGoogle Scholar
  • 13 Jnanaga J. Hirata K. Saeki H. Katsuki T. Yamaguchi M. Bull. Chem. Soc. Jpn.  1979,  52:  1989 
    CrossrefGoogle Scholar
  • 14a Fürstner A. Angew. Chem. Int. Ed.  2000,  39:  3012 
    Google Scholar
  • 14b Liu D. Kozmin SS. Org. Lett.  2002,  4:  3005 
    Google Scholar
  • 14c Prunet J. Angew. Chem. Int. Ed.  2003,  42:  2826 
    Google Scholar
  • 14d Garica-Fortanet J. Murga J. Falomir E. Carda M. Marco JA. J. Org. Chem.  2005,  70:  9822 
    Google Scholar
  • 14e Gradillas A. Perez-Castells J. Angew. Chem. Int. Ed.  2006,  45:  6086 
    Google Scholar
  • The coupling constant value of JH5-H6 = 15.8 Hz in the multiplet at δ = 5.59-5.76 confirmed the trans geometry.
  • 15a Hori H. Nishida Y. Ohrui H. Meguro H. J. Org. Chem.  1989,  54:  1346 
    Google Scholar
  • 15b Sharma GVM. Janardhan Reddy J. Laxmi Reddy K. Tetrahedron Lett.  2006,  47:  6531 
    Google Scholar