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Synlett 2005(3): 437-440
DOI: 10.1055/s-2004-837221
DOI: 10.1055/s-2004-837221
LETTER
© Georg Thieme Verlag Stuttgart · New York
First Total Synthesis of Caminoside A, an Antimicrobial Glycolipid from Sponge
Further Information
Received
18 November 2004
Publication Date:
22 December 2004 (online)
Publication History
Publication Date:
22 December 2004 (online)
Abstract
Caminoside A, a novel antimicrobial tetrasaccharide glycolipid from the marine sponge Caminus sphaeroconia, which represents the first bacterial type III secretion inhibitor, is synthesized in a total of 57 steps starting from d-glucose, d-galactose, l-rhamnose, and 9-decenal.
Key words
caminoside A - d-glucose - d-galactose
- 1
Linington RG.Robertson M.Gauthier A.Finlay BB.van Soest R.Andersen RJ. Org. Lett. 2002, 4: 4089 -
2a
Wada T.Ohkabso A.Mochizuki A.Sekine M. Tetrahedron Lett. 2001, 42: 1069 -
2b
Love KR.Andradego RB.Seeberger PH. J. Org. Chem. 2001, 66: 8165 -
3a
Schmidt RR.Toepfer A. Tetrahedron Lett. 1991, 32: 3353 -
3b
Han X.Schmidt RR. Liebigs Ann. Chem. 1992, 817 -
4a
Fairbanks AJ. Synlett 2003, 1945 -
4b
Crich D.Sun S. J. Am. Chem. Soc. 1997, 119: 11217 - 5
Zhu T.Boons G.-J. Org. Lett. 2001, 3: 4201 -
6a
Liu KK.-C.Danishefsky SJ. J. Org. Chem. 1994, 59: 1892 -
6b
Lichtenthaler FW.Schneider-Adams T. J. Org. Chem. 1994, 59: 6728 -
7a
Banoub J.Boullanger P.Potier M.Descotes G. Tetrahedron Lett. 1986, 27: 4145 -
7b
Trumtel M.Tavecchia P.Veyrieres A.Sinaӱ P. Carbohydr. Res. 1989, 191: 29 -
7c
Wotovic A.Jacquinet J.-C.Sinaӱ P. Carbohydr. Res. 1990, 205: 235 -
8a
Yu B.Tao H. Tetrahedron Lett. 2001, 42: 2405 -
8b
Yu B.Tao H. J. Org. Chem. 2002, 67: 9099 -
8c
Adinolfi M.Iadonisi A.Ravida A.Schiattarella M. Synlett 2004, 275 - 9
Takeo K.Nakaji T.Shinmitsu K. Carbohydr. Res. 1984, 133: 275 - 10
Lee YS.Rho ES.Min YK.Kim BT.Kim KH. J. Carbohydr. Chem. 2001, 20: 503 - 11
Ogawa T.Yamamoto H. Agric. Biol. Chem. 1985, 49: 475 - 12
Lerner LM. Carbohydr. Res. 1993, 241: 291 -
13a
Zegelaar-Jaarsveld K.van der Plas SC.van der Marel GA.van Boom JH. J. Carbohydr. Chem. 1996, 15: 591 -
13b
Zhang Z.Magnusson G. Carbohydr. Res. 1994, 262: 79 -
14a
Bilik V.Voelter W.Bayer E. Angew. Chem., Int. Ed. Engl. 1971, 10: 909 -
14b
Lichtenthaler FW.Metz T. Eur. J. Org. Chem. 2003, 3081 -
15a
Konradsson P.Udodong UE.Fraser-Reid B. Tetrahedron Lett. 1990, 31: 4313 -
15b
Hunt DK.Seeberger PH. Org. Lett. 2002, 4: 2751 - 16
Banwell MG.McRae KJ. Org. Lett. 2000, 2: 3583 - 17
Holm T. J. Chem. Soc., Perkin Trans. 2 1981, 464 -
18a
Smith AB.Cho YS.Friestad GK. Tetrahedron Lett. 1998, 39: 8765 -
18b
Nicolaou KC.Gray D.Tea J. Angew. Chem. Int. Ed. 2001, 3675 - 19
Wessel H.-P.Ivesen T.Bundle DR. J. Chem. Soc., Perkin Trans. 1 1985, 2247 - 20 For a recent account, see:
Fraser-Raid B.López JC.Gómez AM.Uriel C. Eur. J. Org. Chem. 2004, 1387 - 21 The stereochemistry of the aglycone was determined recently, see:
MacMillan JB.Linington RG.Andersen RJ.Molinski TF. Angew. Chem. Int. Ed. 2004, 43: 5946