Synthesis of 1,6-Ansaglycosides

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

References

• 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, and Sato 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

1

Present address: Department of Chemistry, Stanford University, Mudd Building, 333 Campus Drive, Stanford, CA 94305-5080, USA.