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 2003(8): 1253-1261
DOI: 10.1055/s-2003-39404
DOI: 10.1055/s-2003-39404
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York
Synthesis of 1,6-Ansaglycosides
Further Information
Received
6 February 2003
Publication Date:
26 May 2003 (online)
Publication History
Publication Date:
26 May 2003 (online)
Abstract
Two representatives of the 1,6-ansaglycoside class of compounds have been synthesized by different ring-closing strategies.
Key words
ansa compounds - ring closure - macrocycles - glycosides - carbohydrates - total synthesis - natural products
- 2 Review:
Zinsmeister HD.Becker H.Eicher T. Angew. Chem., Int. Ed. Engl. 1991, 30: 130; Angew. Chem. 1991, 103: 134 - 3
Cullmann F. Dissertation Universität des Saarlandes; Germany: 1996. - 4
Schoeneborn R. Dissertation Universität des Saarlandes; Germany: 1996. - 5
Mues R.Huneck S.Connolly JD.Rycroft DS. Tetrahedron Lett. 1986, 29: 6793 - 6
Ogiso A.Sato A.Kashida I.Kuwano H. Chem. Pharm. Bull. 1974, 22: 135 - 7
Ogiso A, andSato A. inventors; Jpn. Pat. Appl. JP48052912. ; Chem. Abstr. 1974, 80, 19537 - 8
Reynolds WW.Evans DL. Org. Synth., Coll. Vol. III Wiley; London: 1955. p.432 - 9
Dalcanale E.Montanari F. J. Org. Chem. 1986, 51: 567 - 10
Excoffier G.Gagnaire D.Utille JP. Carbohydr. Res. 1975, 39: 368 - 11
Pearlman WM. Tetrahedron Lett. 1967, 8: 1663 - 12
Inaga J.Hirata K.Saeki H.Katsuki T.Yamaguchi M. Bull. Chem. Soc. Jpn. 1979, 52: 989 - 13
Boden EP.Keck GE. J. Org. Chem. 1980, 50: 2394 - 14
Mukaiyama T.Usui M.Saigo K. Chem. Lett. 1976, 49 - 15
Kurihara T.Nakajima Y.Mitsunobu O. Tetrahedron Lett. 1976, 28: 2455 - 16
Mukaiyama T.Usui M.Shimada F.Saigo K. Chem. Lett. 1975, 1045 - 17
Kita Y.Maeda H.Takahashi F.Fukui S.Ogawa T.Hatayama K. Chem. Pharm. Bull. 1994, 42: 147 - 18
Brown GR.Foubister AJ.Freeman S.McTaggart F.Mirrlees DJ. Bioorg. Med. Chem. Lett. 1994, 7: 597 - 19
Li T.Hilton S.Janda KD. J. Am. Chem. Soc. 1995, 117: 2123 - 20 While this work was in progress,
Schmidt et al. reported an intramolecular glycosylation strategy
for the α- or β-diastereoselective synthesis of O-glycosides from thioglycosides making
use of xylyl protecting groups as a tether for the glycosyl donor
and acceptor. In so far ansaglycosides according to the definition
in the text were intermediates in their work on the way to the target
acyclic glycosides, see:
Müller M.Huchel U.Geyer A.Schmidt RR. J. Org. Chem. 1999, 64: 6190 - 21
Pfizer, Chas and Co. Inc . inventors; Ger. Pat. Appl. DE1912416. ; Chem. Abstr. 1970, 72, 66951d
References
Present address: Department of Chemistry, Stanford University, Mudd Building, 333 Campus Drive, Stanford, CA 94305-5080, USA.