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Synthesis 2011(20): 3343-3349  
DOI: 10.1055/s-0030-1260174
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Total Synthesis of Achaetolide from l-Malic Acid

Gowravaram Sabitha*, Rangavajjula Srinivas, Jhillu S. Yadav
Division of Organic Chemistry, Indian Institute of Chemical Technology (CSIR), Hyderabad 500 607, India
Fax: +91(40)27160512; e-Mail: gowravaramsr@yahoo.com; e-Mail: sabitha@iict.res.in;
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Publication History

Received 6 June 2011
Publication Date:
16 August 2011 (online)

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Abstract

A convergent total synthesis of achaetolide is described. The key steps include a Horner-Wadsworth-Emmons olefination, CBS reduction to install the stereochemistry at the C9 center, ste­reoselective vinylation to introduce the chiral center at C6, and finally­ a ring-closing metathesis (RCM) reaction to construct the ten-membered lactone of the molecule.

Key words

macrocycles - metathesis - stereoselective synthesis - reduction­ - olefination

    References

  • 2 Bodo B. Molho L. Davoust D. Molho D. Phytochemistry  1983,  22:  447 
    CrossrefGoogle Scholar
  • 3 Tayone WC. Shindo S. Murakami T. Hashimoto M. Tanaka K. Noboru Takada N. Tetrahedron  2009,  65:  7464 
    CrossrefGoogle Scholar
  • 4a Fuchser J. Zeeck A. Liebigs Ann./Recueil  1997,  87 
    Google Scholar
  • 4b Grabley S. Granzer E. Hütter K. Ludwig D. Mayer M. Thiericke R. Till G. Wink J. Hoechst AG. Phillips S. Zeeck A. J. Antibiot.  1992,  45:  56 
    Google Scholar
  • 4c Göhrt A. Zeeck A. Hütter K. Thiericke R. Kirsch R. Kluge H. J. Antibiot.  1992,  45:  66 
    Google Scholar
  • 4d Grabley S. Hammann P. Hütter K. Kirsch R. Kluge H. Thiericke R. Hoechst AG. Mayer M. Zeeck A. J. Antibiot.  1992,  45:  1176 
    Google Scholar
  • 4e Ayer WA. Sun M. Browne LM. Brinen LS. Clardy J. J. Nat. Prod.  1992,  55:  649 
    Google Scholar
  • 4f Ratnayake AS. Yoshida WY. Mooberry SL. Hemscheidt T. Org. Lett.  2001,  3:  3479 
    Google Scholar
  • 4g Fürstner A. Radkowski K. Chem. Commun.  2001,  671 
    Google Scholar
  • 4h Fürstner A. Radkowski K. Wirtz C. Goddard R. Lehmann CW. Mynott R. J. Am. Chem. Soc.  2002,  124:  7061 
    Google Scholar
  • 5 Dräger G. Kirschning A. Thiericke R. Zerlin M. Nat. Prod. Rep.  1996,  13:  365 
    CrossrefGoogle Scholar
  • 6a Chandrasekhar S. Balaj SV. Rajesh G. Tetrahedron Lett.  2010,  51:  5164 
    Google Scholar
  • 6b Das T. Rajib B. Samik N. Tertrahedron: Asymmetry  2010,  21:  2206 
    Google Scholar
  • 6c Srihari P. Kumaraswamy B. Sankar P. Ravishashidhar V. Yadav JS. Tetrahedron Lett.  2010,  51:  6174 
    Google Scholar
  • 6d Rao SK. Amit Kumar C. Ghosh S. Synlett  2010,  3078 
    Google Scholar
  • 7a Sabitha G. Yadagiri K. Swapna R. Yadav JS. Tetrahedron Lett.  2009,  50:  5417 
    Google Scholar
  • 7b Sabitha G. Padmaja P. Reddy NP. Jadav SS. Yadav JS. Tetrahedron Lett.  2010,  51:  6166 
    Google Scholar
  • 7c Sabitha G. Srinivas C. Maruthi C. Yadav JS. Helv. Chim. Acta  2010,  93:  1634 
    Google Scholar
  • 7d Sabitha G. Reddy TR. Srinivas C. Yadav JS. Helv. Chim. Acta  2011,  94:  224 
    Google Scholar
  • 7e Sabitha G. Reddy TR. Ramesh M. Srinivas C. Yadav JS. Bull. Chem. Soc. Jpn.  2011,  84:  229 
    Google Scholar
  • 8a Saito S. Ishikawa T. Kuroda A. Koga K. Moriwake T. Tetrahedron  1992,  48:  4067 
    Google Scholar
  • 8b Boukouvalas J. Fortier G. Radu I.-I. J. Org. Chem.  1998,  63:  916 
    Google Scholar
  • 9a Heathcock CH. Hadley CR. Rosen T. Theisen PD. Hecker SJ. J. Med. Chem.  1987,  30:  1858 
    Google Scholar
  • 9b Yasuda N. Hsiao Y. Jensen MS. Rivera NR. Yang C. Wells KM. Yau J. Palucki M. Tan L. Dormer PG. Volante RP. Hughes DL. Reider PJ. J. Org. Chem.  2004,  69:  1959 
    Google Scholar
  • 10a Alvarez-Ibarra C. Arias S. Banon G. Fernandez M. Rodriguez V. Sinisterra VJ. J. Chem. Soc., Chem. Commun.  1987,  1509 
    Google Scholar
  • 10b Paterson I. Yeung KS. Smail JB. Synlett  1993,  774 
    Google Scholar
  • 11 Corey EJ. Bakshi RK. Shibata S. Chen C.-P. Singh VK. J. Am. Chem. Soc.  1987,  109:  7925 
    CrossrefGoogle Scholar
  • 12a Reetz MT. Acc. Chem. Res.  1993,  26:  462 
    Google Scholar
  • 12b Mendgel A. Reiser O. Chem. Rev.  1999,  99:  1191 
    Google Scholar
  • 13 Simpson TJ. Smith RW. Westaway SM. Willis CL. Tetrahedron Lett.  1997,  38:  5367 
    CrossrefGoogle Scholar
  • 14 Alcaraz L. Harnett JJ. Mioskowski C. Martel JP. Legall T. Shin D.-S. Falck JR. Tetrahedron Lett.  1994,  35:  5449 
    CrossrefGoogle Scholar
  • 15 Solladie G. G ressot-Kempf L. Tetrahedron: Asymmetry  1996,  7:  1753 
    CrossrefGoogle Scholar
  • 16a Grubbs RH. Miller SJ. Fu GC. Acc. Chem. Res.  1995,  28:  446 
    Google Scholar
  • 16b Prunet J. Angew. Chem. Int. Ed.  2003,  42:  2826 
    Google Scholar
  • 16c Schwab P. Grubbs RH. Ziller JW. J. Am. Chem. Soc.  1996,  118:  100 
    Google Scholar
  • 16d Giri AG. Mondal MA. Puranik VG. Ramana CV. Org. Biomol. Chem.  2010,  8:  398 
    Google Scholar
1

Visiting Professor, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.