Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2009(3): 372-374
DOI: 10.1055/s-0028-1083310
DOI: 10.1055/s-0028-1083310
SHORTPAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Total Synthesis of (±)-1,3,4,5-Tetragalloylapiitol
Further Information
Received
29 September 2008
Publication Date:
09 January 2009 (online)
Publication History
Publication Date:
09 January 2009 (online)
Abstract
Starting from citraconic anhydride, the first total synthesis of (±)-1,3,4,5-tetragalloylapiitol has been demonstrated via a stepwise route involving generation of an apiitol derivative followed by benzoylation.
Key words
allylic hydroxylation - osmium tetroxide - natural products - (±)-1,3,4,5-tetragalloylapiitol
- 1
Kohlstaedt LA.Wang J.Friedman JM.Rice PA.Steitz TA. Science 1992, 256: 1783 - 2
Arnold E.Jacobo-Molina A.Nanni RG.Williams RL.Lu X.Ding J.Clark AD.Zhang A.Ferris AL.Clark P.Hizi A.Hughes SH. Nature 1992, 357: 85 - 3
Imamichi T. Curr. Pharm. Des. 2004, 10: 4039 - 4
Takada K.Bermingham A.O’Keefe BR.Wamiru A.Beutler JA.Le Grice SFJ.Lloyd J.Gustafson KR.McMahon JB. J. Nat. Prod. 2007, 70: 1647 - 5
Witczak JZ.Whistler RL.Daniel JR. Carbohydr. Res. 1984, 133: 235 - 6
Kar A.Argade NP. J. Org. Chem. 2002, 67: 7131 - 7
Ren Y.Himmeldirk K.Chen X. J. Med. Chem. 2006, 49: 2829 - 8 For a recent synthesis of an analogous
natural product, sanguiin H-5, see:
Su X.Surry DS.Spandl RJ.Spring DR. Org. Lett. 2008, 10: 2593