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Synthesis 2011(5): 821-825  
DOI: 10.1055/s-0030-1259431
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Total Synthesis of (+)-Goniodiol

Gowravaram Sabitha*, M. Bhikshapathi, N. Ranjith, N. Ashwini, Jhillu S. Yadav
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: gowravaramsr@yahoo.com; e-Mail: sabitha@iict.res.in;
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Publication History

Received 29 November 2010
Publication Date:
31 January 2011 (online)

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Abstract

An efficient total synthesis of (+)-goniodiol was illustrated by using Carreira alkynylation and Sharpless asymmetric dihydroxylation as key steps.

Key words

styryl lactones - goniodiol - Carreira alkynylation - Sharpless asymmetric dihydroxylation

    References

  • 1a Mu Q. Tang WD. Liu RY. Li CM. Lou LG. Sun HD. Planta Med.  2003,  69:  826 
    Google Scholar
  • 1b Pihie AH. Stanslas J. Din LB. Anticancer Res.  1998,  18:  1739 
    Google Scholar
  • 2a Wu YC. Duh CY. Chang FR. Wang SK. Chang JJ. McPhail DR. McPhail AT. Lee KH. J. Nat. Prod.  1991,  54:  1077 
    Google Scholar
  • 2b Sam TW. Saw-Yeu C. Matsjeh S. Gan EK. Razak D. Mohamed AL. Tetrahedron Lett.  1987,  28:  2541 
    Google Scholar
  • 2c Talapatra SK. Basu D. Goaswami S. Talapatra B. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1985,  24:  29 
    Google Scholar
  • 2d Alkofahi A. Ma WW. Mckenze AT. Byrn SR. Mclaughlin JL. J. Nat. Prod.  1989,  52:  1371 
    Google Scholar
  • 2e Fang XP. Anderson JE. Qui XX. Kozlowski JF. Mclaughlin JL. Tetrahedron  1993,  49:  1563 
    Google Scholar
  • 3 Fang XP. Anderson JE. Chang CJ. Mclaughlin JL. Fanwick PE. J. Nat. Prod.  1991,  54:  1034 
    CrossrefGoogle Scholar
  • 4 Nakashima K. Kikuchi N. Shirayama D. Miki T. Ando K. Sono M. Suzuki S. Kawasw M. Kondoh M. Sato M. Kanai K. Nagase H. Honda T. Bull. Chem. Soc. Jpn.  2007,  80:  387 
    CrossrefGoogle Scholar
  • 5 Tsubuki M. Kanai K. Nagase H. Honda T. Tetrahedron  1999,  55:  2493 
    CrossrefGoogle Scholar
  • 6a Tsubiki M. Kanai K. Honda T. J. Chem. Soc., Chem. Commun.  1992,  1640 
    Google Scholar
  • 6b Annaick F. Francois C. Michael D. Bertrand C. Eur. J. Org. Chem.  2008,  29:  4900 
    Google Scholar
  • 6c Mukai C. Hirai S. Hanaoka M. J. Org. Chem.  1997,  62:  6619 
    Google Scholar
  • 6d Surivet JP. Goré J. Vatèle JM. Tetrahedron  1996,  37:  14877 
    Google Scholar
  • 6e Prasad KR. Gholap SL. Tetrahedron Lett.  2007,  48:  4679 
    Google Scholar
  • 6f Tsubuki M. Kanai K. Nagase H. Honda T. Tetrahedron  1999,  55:  2493 
    Google Scholar
  • 6g Surivet JP. Vetele JM. Tetrahedron Lett.  1998,  39:  7299 
    Google Scholar
  • 6h Edward TW. Darren DJ. Steven LV. Org. Biomol. Chem.  2006,  4:  1698 
    Google Scholar
  • 6i Ramachandran PV. Subash CJ. Reddy MV. J. Org. Chem.  2002,  67:  7547 
    Google Scholar
  • 7a Chen J. Lin G.-Q. Wang Z.-M. Liu H.-Q. Synlett  2002,  1265 
    Google Scholar
  • 7b Banwell MG. Coster MJ. Karunaratne OP. Smith JA. J. Chem. Soc., Perkin Trans. 1  2002,  1622 
    Google Scholar
  • 7c Yadav JS. Krishna VH. Srilatha A. Somaiah R. Reddy BV. Synthesis  2010,  3004 
    Google Scholar
  • 7d Yadav JS. Premalatha K. Harshavardhan S. Reddy BV. Tetrahedron Lett.  2008,  49:  6765 
    Google Scholar
  • 8a Sabitha G. Sudhakar K. Yadav JS. Synthesis  2007,  385 
    Google Scholar
  • 8b Sabitha G. Narjis F. Gopal P. Reddy CN. Yadav JS. Tetrahedron: Asymmetry  2009,  20:  184 
    Google Scholar
  • 8c Sabitha G. Prasad MN. Shankaraiah KS. Jadav JS. Synthesis  2010,  1171 
    Google Scholar
  • 8d Sabitha G. Bhaskar V. Reddy SSS. Yadav JS. Helv. Chim. Acta  2010,  93:  329 
    Google Scholar
  • 9a Boyall D. Frantz DE. Carreira EM. Org. Lett.  2002,  4:  2605 
    Google Scholar
  • 9b Fettes A. Carreira EM. J. Org. Chem.  2003,  68:  9274 
    Google Scholar
  • 10 Serrat X. Cabarrocas G. Ventura M. Linden A. Villalgordo JM. Tetrahedron: Asymmetry  1999,  10:  3417 
    CrossrefGoogle Scholar
  • 11a Wendt KU. Schulz GE. Liu DR. Corey EJ. Angew. Chem. Int. Ed.  2000,  39:  2812 
    Google Scholar
  • 11b Corey EJ. Shibata S. Bakshi RK. J. Org. Chem.  1988,  53:  2861 
    Google Scholar
  • 11c Scheerer JR. Lawrence JF. Wang GC. Evans DA. J. Am. Chem. Soc.  2007,  129:  8968 
    Google Scholar
  • 12 Yadav JS. Bandhopadhayaya A. Kunwar AC. Tetrahedron Lett.  2001,  42:  4907 
    CrossrefGoogle Scholar
  • 13 Li L.-S. Wu Y.-L. Tetrahedron  2002,  58:  9049 
    CrossrefGoogle Scholar
  • 14 Kolb HC. VanNieuwenhze MS. Sharpless KB. Chem. Rev.  1994,  94:  2483 
    Google Scholar
  • 15 Oikawa Y. Yoshioka T. Yonemitsu O. Tetrahedron Lett.  1982,  23:  889 
    CrossrefGoogle Scholar
  • 16 Pang J.-H. Ham Y.-J. Lee D.-H. Bull. Korean Chem. Soc.  2003,  24:  891 
    CrossrefGoogle Scholar
  • 17 Dess DB. Martin JC. J. Org. Chem.  2004,  69:  2091 
    Google Scholar
  • 18 Still WC. Gennari C. Tetrahedron Lett.  1983,  24:  4405 
    CrossrefGoogle Scholar