Stereochemical features of the [1,2]-Wittig rearrangement of O- glycosides derived from D-galactono- and D-xylono-γ-lactones: A new approach to the core part of zaragozic acids

Tetrahedron Letters

Volumn 40, Issue 10, 1999, Pages 1917-1920

  Tomooka, K ^a   Kikuchi, M ^a   Igawa, K ^a   Keong, P H ^a   Nakai, T ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Asymmetric synthesis; Glycosides; Rearrangement; Zaragozic acids

Indexed keywords

DEXTRO GALACTONO GAMMA LACTONE; DEXTRO XYLONO GAMMA LACTONE; GAMMA LACTONE DERIVATIVE; GLYCOSIDE; UNCLASSIFIED DRUG; ZARAGOZIC ACID A;

ARTICLE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033525664     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00043-X     Document Type: Article

References (13)

1. K. Tomooka T. Nakai J. Synth. Org. Chem. Jpn. 54 1996 1000 1008
2. K. Tomooka H. Yamamoto T. Nakai Liebig Ann./ Recl. 1997 1275 1281
3. K. Tomooka H. Yamamoto T. Nakai J. Am. Chem. Soc. 118 1996 3317 3318
4. For a recent review on C -glycosidation, see: D. Levy C. Tang The Chemistry of C -Glycosides 1995 Pergamon
5. Y.G. Du R.J. Linhardt I.R. Valhov Tetrahedron 54 1998 9913 9959
6. Review: A. Nadin K.C. Nicolaou Angew. Chem., Int. Ed. Engl. 35 1996 1623 1656
7. Isolation: M.J. Dawson J.E. Farthing P.S. Marthall R.F. Middleton M.J. O'Neill A. Shuttleworth C. Stylli R.M. Tait P.M. Taylor H.G. Widman A.D. Buss D. Langley M.V. Hayes J. Antibiot. 45 1992 639 647
8. K.E. Wilson R.M. Burk T. Biftu R.G. Ball K. Hoogsteen J. Org. Chem. 57 1992 7151 7158
9. Total synthesis: K.C. Nicolaou A. Nadin J.E. Leresche E.W. Yue S. Lagreca Angew. Chem., Int. Ed. Engl. 33 1994 2190 2191
10. S. Caron D. Stoermer A.K. Mapp C.H. Heathcock J. Org. Chem. 61 1996 9126 9134
11. B.M. Trost E.D. Edstrom Angew. Chem., Int. Ed. Engl. 29 1990 520 521
12. K. Tomooka Y. Nakamura T. Nakai Synlett 1995 321 322
13. The [1,2]-Wittig rearrangement is well recognized to proceed via the radical dissociation-recombination mechanism: see U. Schöllkopf Angew. Chem., Int. Ed. Engl. 9 1970 763 773 and ref. 2