Download PDF
Synthesis 2011(22): 3706-3710  
DOI: 10.1055/s-0030-1260246
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Stereoselective Total Synthesis of (+)-Cryptofolione and the First Synthesis of (-)-Cryptocaryalactone [¹]

P. Balasubramanyam, Gandolla Chinna Reddy, Nayaki Salvanna, Biswanath Das*
Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: biswanathdas@yahoo.com;
Further Information

Publication History

Received 1 July 2011
Publication Date:
29 September 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

The stereoselective syntheses of the naturally occurring α-pyrone derivatives (+)-cryptofolione and (-)-cryptocaryalactone were efficiently accomplished by using propane-1,3-diol as the starting material. Keck allylation, Mitsunobu center inversion, and olefin cross metathesis were used as the key steps. (-)-Cryptocarya­lactone was synthesized here for the first time.

Key words

total synthesis - lactones - natural products - Keck allylation - Mitsunobu center inversion - olefin cross metathesis

1

Part 51 in the series ‘Synthetic Studies on Natural Products’

    References

  • 2a Rychnovsky SD. Chem. Rev.  1995,  95:  2021 
    Google Scholar
  • 2b Jodynis-Liebert J. Murias M. Bloszyk E. Planta Med.  2000,  66:  199 
    Google Scholar
  • 2c Murga J. Falomir E. Marco JA. Org. Lett.  2002,  4:  3447 
    Google Scholar
  • 2d Hagen S. Vara Prasad JVN. Tait BD. Adv. Med. Chem.  2000,  5:  159 
    Google Scholar
  • 2e Inayat-Hussain SH. Annuar BO. Din LB. Ali AM. Ross D. Toxicol. in Vitro  2003,  17:  433 
    Google Scholar
  • 3a Kalesse M. Christmann M. Bhatt U. Quitschalle M. Claus E. Saeed A. Burzlaff A. Kasper C. Haustedt LO. Hofer E. Scheper T. Beil W. ChemBioChem  2001,  2:  709 
    Google Scholar
  • 3b Kalesse M. Christmann M. Synthesis  2002,  981 
    Google Scholar
  • 3c Bialy L. Waldmann H. Chem. Commun.  2003,  1872 
    Google Scholar
  • 3d Buck SB. Hardouin C. Ichikawa S. Soenen DR. Gauss C.-M. Hwang I. Swingle MR. Bonness KM. Honkanen RE. Boger DL. J. Am. Chem. Soc.  2003,  125:  15694 
    Google Scholar
  • 4a Bohlmann F. Suwita A. Phytochemistry  1979,  18:  677 
    Google Scholar
  • 4b Juliawata LD. Kitajima M. Takayama H. Achmad SA. Aimi N. Phytochemistry  2000,  54:  989 
    Google Scholar
  • 4c Drewes SE. Sehlapelo BM. Horn MM. Scott-Shaw R. Sander O. Phytochemistry  1995,  38:  1427 
    Google Scholar
  • 4d Drewes SE. Horn MM. Scott-Shaw R. Phytochemistry  1995,  40:  321 
    Google Scholar
  • 5a Sehlapelo BM. Drewes SE. Scott-Shaw R. Phytochemistry  1994,  37:  847 
    Google Scholar
  • 5b Cavalheiro AJ. Yoshida M. Jodynis-Liebert J. Murias M. Bloszyk E. Phytochemistry  2000,  53:  811 
    Google Scholar
  • 6a Zschocke S. Van Staden JJ. Ethnopharmacology  2000,  71:  473 
    Google Scholar
  • 6b Drewes SE. Horn MH. Mavi S. Phytochemistry  1997,  44:  437 
    Google Scholar
  • 7 Schemda-Hirschmann G. Astuddillo L. Bastida J. Codina C. De Arias AR. Ferrira ME. Inchaustti A. Yaluff G. J. Pharm. Pharmacol.  2001,  53:  563 
    CrossrefGoogle Scholar
  • 8 Sturgeon CM. Cinel B. Diaz-Marrero AR. McHardy LM. Ngo M. Andersen RJ. Roberge M. Cancer Chemother. Pharmacol.  2008,  61:  407 
    CrossrefGoogle Scholar
  • 9a Matsuoka Y. Aikawa K. Irie R. Katsuki T. Heterocycles  2005,  66:  187 
    Google Scholar
  • 9b Sabitha G. Reddy SSS. Reddy DV. Bhaskar V. Yadav JS. Synthesis  2010,  3453 
    Google Scholar
  • 9c Kumar RN. Mesham HM. Tetrahedron Lett.  2011,  52:  1003 
    Google Scholar
  • 9d Das B. Nagendra S. Reddy CR. Tetrahedron: Asymmetry  2011,  22:  1249 
    Google Scholar
  • 10a Spencer GF. England RE. Wolf RB. Phytochemistry  1984,  23:  2499 
    Google Scholar
  • 10b Drewes SE. Horn MM. Ramesar NS. Ferreira D. Nel RJ.-J. Hutchings A. Phytochemistry  1998,  49:  1683 
    Google Scholar
  • 11a Mori Y. Furukawa H. Chem. Pharm. Bull.  1994,  42:  2161 
    Google Scholar
  • 11b Sabitha G. Bhaskar V. Reddy SSS. Yadav JS. Tetrahedron  2008,  64:  10207 
    Google Scholar
  • 11c Radhakrishna P. Krishnarao L. Reddy KLN. Beilstein J. Org. Chem.  2009,  5:  14 
    Google Scholar
  • 11d Sabitha G. Bhaskar V. Reddy SSS. Helv. Chim. Acta  2010,  93:  329 
    Google Scholar
  • 12a Das B. Veeranjaneyulu B. Balasubramanyam P. Srilatha M. Tetrahedron: Asymmetry  2010,  21:  2762 
    Google Scholar
  • 12b Das B. Balsubramanyam P. Veeranjaneyulu B. Reddy GC. Helv. Chim. Acta  2011,  94:  881 
    Google Scholar
  • 13 Keck GE. Tarbet KH. Geraci LS. J. Am. Chem. Soc.  1993,  115:  8467 
    CrossrefGoogle Scholar
  • 14 Mitsunobu O. Synthesis  1981,  1 
    Article in Thieme ConnectGoogle Scholar
  • 15 Rychnovsky D. Skalitzky DJ. Tetrahedron Lett.  1990,  31:  945 
    CrossrefGoogle Scholar
  • 16a Grubbs RH. Chang S. Tetrahedron  1998,  54:  4413 
    Google Scholar
  • 16b Grubbs RH. Tetrahedron  2004,  60:  7117 
    Google Scholar
1

Part 51 in the series ‘Synthetic Studies on Natural Products’