Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen

IMPACT FACTOR 2017: 5.294

CiteScore 2017: 3.42

SCImago Journal Rank (SJR) 2017: 1.212
Source Normalized Impact per Paper (SNIP) 2017: 1.546

See all formats and pricing
More options …
Volume 84, Issue 7


Spiroketals: Toward the synthesis of 39-oxobistramide K

Malgorzata Commandeur
  • Corresponding author
  • Laboratoire de Chimie Organique Associé au CNRS, ESPCI ParisTech, 10 rue Vauquelin, 75231 Paris Cedex 05, France
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Claude Commandeur
  • Corresponding author
  • Laboratoire de Chimie Organique Associé au CNRS, ESPCI ParisTech, 10 rue Vauquelin, 75231 Paris Cedex 05, France
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Janine Cossy
  • Corresponding author
  • Laboratoire de Chimie Organique Associé au CNRS, ESPCI ParisTech, 10 rue Vauquelin, 75231 Paris Cedex 05, France
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2012-02-28 | DOI: https://doi.org/10.1351/PAC-CON-11-09-06

An advanced spiroketal intermediate toward the synthesis of 39-oxobistramide K was prepared, fragment C14–C40. This fragment was obtained in 19 steps with an overall yield of 6.2 % using a FeCl3-catalyzed spiroketalization as the key step.

Keywords: cyclizations; organic synthesis; spiroketalization


International Conference on Heterocyclic Chemistry (ICHC-23), International Congress on Heterocyclic Chemistry, ICHC, Heterocyclic Chemistry, 23rd, Glasgow, UK, 2011-07-31–2011-08-04


  • 1a

    , C. Bolm, J. Legros, J. Le Paih, L. Zani. Chem. Rev.104, 6217 (2004).CrossrefGoogle Scholar

  • 1b

    , C.-L. Sun, B.-J. Li, Z.-J. Shi. Chem. Rev.111, 1293 (2011).CrossrefGoogle Scholar

  • 2

    , B. T. Murphy, S. Cao, P. Brodie, J. Maharavo, H. Andriamanantoanina, P. Ravelonandro, D. G. Kingston. J. Nat. Prod.72, 1338 (2009).CrossrefGoogle Scholar

  • 3a

    , F. Perron, K. F. Albizati. Chem. Rev.89, 1617 (1989).CrossrefGoogle Scholar

  • 3b

    , M. T. Fletcher, W. Kitching. Chem. Rev.95, 789 (1995).CrossrefGoogle Scholar

  • 3c

    M. F. Jacobs, W. Kitching. Curr. Org. Chem.2, 395 (1998).Google Scholar

  • 3d

    , S. Favre, P. Vogel, S. Gerber-Lemaire. Molecules13, 2570 (2008).CrossrefGoogle Scholar

  • 4a

    , A. F. Kluge. Heterocycles24, 1699 (1986).CrossrefGoogle Scholar

  • 4b

    V. Vaillancourt, N. E. Pratt, K. F. Albizati. The Total Synthesis of Natural Products, John Wiley, New York (1992).Google Scholar

  • 4c

    , K. T. Mead, B. N. Brewer. Curr. Org. Chem.7, 227 (2003).CrossrefGoogle Scholar

  • 4d

    , M. A. Brimble, D. P. Furkert. Curr. Org. Chem.7, 1461 (2003).CrossrefGoogle Scholar

  • 4e

    , J. E. Aho, P. M. Pihko, T. K. Rissa. Chem. Rev.105, 4406 (2005).CrossrefGoogle Scholar

  • 4f

    , G. Zinzalla, L.-G. Milroy, S. V. Ley. Org. Biomol. Chem.4, 1977 (2006).CrossrefGoogle Scholar

  • 4g

    , B. R. Raju, A. K. Saikia. Molecules13, 1942 (2008).CrossrefGoogle Scholar

  • 5

    , D. Bondar, J. Liu, T. Müller, L. A. Paquette. Org. Lett.7, 1813 (2005).CrossrefGoogle Scholar

  • 6

    , N. Pothier, S. Goldstein, P. Deslongchamps. Helv. Chim. Acta75, 604 (1992).CrossrefGoogle Scholar

  • 7

    , J. Sperry, Y.-C. Liu, M. A. Brimble. Org. Biomol. Chem.8, 29 (2010).CrossrefGoogle Scholar

  • 8

    , I. Paterson, D. J. Wallace, K. R. Gibson. Tetrahedron Lett.38, 8911 (1997).CrossrefGoogle Scholar

  • 9

    , R. E. Ireland, S. Thaisrivongs, P. H. Dussault. J. Am. Chem. Soc.110, 5768 (1988).CrossrefGoogle Scholar

  • 10a

    , H. Fuwa, M. Sasaki. Org. Lett.10, 2549 (2008).CrossrefGoogle Scholar

  • 10b

    , E. B. Holson, W. R. Roush. Org. Lett.4, 3719 (2002).CrossrefGoogle Scholar

  • 11a

    , W. Kitching, J. A. Lewis, M. T. Fletcher, J. J. De Voss, R. A. I. Drew, C. J. Moore. J. Chem. Soc., Chem. Commun. 855 (1986).CrossrefGoogle Scholar

  • 11b

    , W. Kitching, J. A. Lewis, M. V. Perkins, R. Drew, C. J. Moore, V. Schurig, W. A. König, W. Francke. J. Org. Chem.54, 3893 (1989).CrossrefGoogle Scholar

  • 12a

    , K. Utimoto. Pure Appl. Chem.55, 1845 (1983).CrossrefGoogle Scholar

  • 12b

    , C. V. Ramana, S. B. Suryawanshi, R. G. Gonnade. J. Org. Chem.74, 2842 (2009).CrossrefGoogle Scholar

  • 13a

    , S. Antoniotti, E. Genin, V. Michelet, J.-P. Genêt. J. Am. Chem. Soc.127, 9976 (2005).CrossrefGoogle Scholar

  • 13b

    , Y. Li, F. Zhou, C. J. Forsyth. Angew. Chem., Int. Ed.46, 279 (2007).CrossrefGoogle Scholar

  • 13c

    Y. Zhang, J. Xue, Z. Xin, Z. Xie, Y. Li. Synlett 940 (2008).Google Scholar

  • 13d

    , A. Aponick, C.-Y. Li, J. A. Palmes. Org. Lett.11, 121 (2009).CrossrefGoogle Scholar

  • 14

    , B. Liu, J. K. De Brabander. Org. Lett.8, 4907 (2006).CrossrefGoogle Scholar

  • 15a

    , X. Li, A. R. Chianese, T. Vogel, R. H. Crabtree. Org. Lett.7, 5437 (2005).CrossrefGoogle Scholar

  • 15b

    , B. A. Messerle, K. Q. Vuong. Pure Appl. Chem.78, 385 (2006).CrossrefGoogle Scholar

  • 15c

    , S. Selvaratnam, J. H. H. Ho, P. B. Huleatt, B. A. Messerle, C. L. L. Chai. Tetrahedron Lett.50, 1125 (2009).CrossrefGoogle Scholar

  • 16

    , B. Lastdrager, M. S. M. Timmer, G. A. van de Marel, H. S. Overkleeft. Tetrahedron Lett.46, 6195 (2005).CrossrefGoogle Scholar

  • 17a

    , T. Shimizu, T. Masuda, K. Hiramoto, T. Nakata. Org. Lett2, 2153 (2000).CrossrefGoogle Scholar

  • 17b

    , P. M. Pihko, J. E. Aho. Org. Lett.6, 3849 (2004).CrossrefGoogle Scholar

  • 18

    , A. Guérinot, A. Serra-Muns, C. Gnamm, C. Bensoussan, S. Reymond, J. Cossy. Org. Lett.12, 1808 (2010).CrossrefGoogle Scholar

  • 19a

    , D. Gouiffès, M. Jugé, N. Grimaud, L. Welin, Y. Barbin, D. Laurent, C. Roussakis, J. P. Hénichart, J. F. Verbist. Toxicon26, 1129 (1988); for isolation of bistramide A, see.CrossrefGoogle Scholar

  • 19b

    D. Gouiffès, S. Moreau, N. Helbecque, J. L. Bernier, J. P. Hénichart, Y. Barbin, D. Laurent, J. F. Verbist. Tetrahedron44, 451 (1988) and cited refs.; for isolation of bistratenes, which were deduced to be identical with bistramides, see.CrossrefGoogle Scholar

  • 19c

    , B. M. Degnan, C. J. Hawkins, M. F. Lavin, E. J. McCaffrey, D. L. Parry, D. J. Watters. J. Med. Chem.32, 1354 (1989).CrossrefGoogle Scholar

  • 20

    For isolation of bistramides A–D and K, see.Google Scholar

  • 20a

    , J. F. Biard, C. Roussakis, J. M. Komprobst, D. Gouiffès-Barbin, J. F. Verbist, P. Cotelle, M. P. Foster, C. M. Ireland, C. Debitus. J. Nat. Prod.57, 1336 (1994); for isolation of bistramides D, K, and L, see.CrossrefGoogle Scholar

  • 20b

    J. F. Biard, D. Cortadellas, C. Debitus, D. Laurent, C. Roussakis, J. F. Verbist. WO 9420503 A1 (1994).Google Scholar

  • 21

    , C. Bauder. Eur. J. Org. Chem. 6207 (2010).CrossrefGoogle Scholar

  • 22a

    , A. V. Statsuk, D. Liu, S. A. Kozmin. J. Am. Chem. Soc.126, 9546 (2004).CrossrefGoogle Scholar

  • 22b

    , M. T. Crimmins, A. C. DeBaillie. J. Am. Chem. Soc.128, 4936 (2006).CrossrefGoogle Scholar

  • 23a

    , A. Hafner, R. O. Duthaler, R. Marti, G. Rihs, P. Rhote-Streit, F. Schwarzenbach. J. Am. Chem. Soc.114, 2321 (1992).CrossrefGoogle Scholar

  • 23b

    , J. Cossy, S. Bouzbouz, F. Pradaux, C. Willis, V. Bellosta. Synlett 1595 (2002).CrossrefGoogle Scholar

  • 24

    M. D. Varney, W. H. Romines, C. L. Palmer. U.S. Patent 5,594,139 (20 pp.), Filed 28 July 1994, Issued 14 January 1997.Google Scholar

  • 25

    , F. Freeman, D. S. H. L. Kim, E. Rodriguez. J. Org. Chem.57, 1722 (1992).CrossrefGoogle Scholar

  • 26

    , Allyl acetate 9 was prepared from benzaldehyde via a two-step sequence: a Grignard addition of vinylmagnesium bromide then the acetylation of the obtained alcohol. Procedure inspired by the literature: N. Marion, R. Gealageas, S. P. Nolan. Org. Lett.9, 2653 (2007).CrossrefGoogle Scholar

  • 27a

    , M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs. Org. Lett.1, 953 (1999).CrossrefGoogle Scholar

  • 27b

    , S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda. J. Am. Chem. Soc.122, 8168 (2000).CrossrefGoogle Scholar

  • 28

    Compound 12 was prepared according to the following synthetic sequence: benzylation.Google Scholar

  • 28a

    , U. Widmer. Synthesis 568 (1987); ester reduction.CrossrefGoogle Scholar

  • 28b

    , J. D. White, M. Kawasaki. J. Org. Chem.57, 5292 (1992); bromination.CrossrefGoogle Scholar

  • 28c

    , G.-J. Boons, J. A. Clase, J. C. Lennon, S. V. Ley, J. Staunton. Tetrahedron51, 5417 (1995); preparation of phosphonium salt.CrossrefGoogle Scholar

  • 28d

    , J. T. Lowe, I. E. Wrona, J. S. Panek. Org. Lett.9, 327 (2007).CrossrefGoogle Scholar

  • 29

    , Keto-phosphonate 15 was prepared according to the literature procedure: B. Corbel, L. Medinger, J.-P. Haelters, G. Sturtz. Synthesis 1048 (1985).CrossrefGoogle Scholar

  • 30

    , M. G. Stocksdale, S. Ramurthy, M. J. Miller. J. Org. Chem.63, 1221 (1998).CrossrefGoogle Scholar

About the article

Published Online: 2012-02-28

Published in Print: 2012-02-29

Citation Information: Pure and Applied Chemistry, Volume 84, Issue 7, Pages 1567–1574, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-11-09-06.

Export Citation

© 2013 Walter de Gruyter GmbH, Berlin/Boston.Get Permission

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

Johan Cornil, Laurine Gonnard, Charlélie Bensoussan, Anna Serra-Muns, Christian Gnamm, Claude Commandeur, Malgorzata Commandeur, Sébastien Reymond, Amandine Guérinot, and Janine Cossy
Accounts of Chemical Research, 2015, Volume 48, Number 3, Page 761
Chandrababu Naidu Kona and C.V. Ramana
Tetrahedron, 2014, Volume 70, Number 23, Page 3653
Pierre-Georges Echeverria, Sébastien Prévost, Johan Cornil, Charlène Férard, Sébastien Reymond, Amandine Guérinot, Janine Cossy, Virginie Ratovelomanana-Vidal, and Phannarath Phansavath
Organic Letters, 2014, Volume 16, Number 9, Page 2390

Comments (0)

Please log in or register to comment.
Log in