A Critical Evaluation of the Cationic Coupling of 4-Acetoxy-1,3-Dioxanes

Synlett

Volumn 1996, Issue 6, 1996, Pages 536-538

  Boons, Geert Jan ^a   Eveson, Robert ^a   Smith, Stephen ^b   Stauch, Thomas ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002170624     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5484     Document Type: Article

References (9)

1. S.D. Rychnovsky, D. J. Skalitzky, Synlett, 1995, 555.
2. a) T. Oishi, T. Nakata, Synthesis, 1990, 635;
3. b) S.D. Rychnovsky, Chem. Rev., 1995, 95, 2021.
4. For a review on C-glycosylations see: M.H.D. Postema, Tetrahedron, 1992, 48, 8545.
5. All new compounds gave satisfactory NMR and mass spectroscopic data.
6. Reduction of the double bond and removal of the acetal protecting group with HCl in methanol resulted in the formation of a single isomeric product, thus proving that epimerisation has taken place at C-2.
7. R.D. Dawe, B. Fraser-Reid, J. Chem. Soc., Chem Commun., 1981, 1180.
8. 2); m/z 241 (53%, [M + 1]).
9. C. Chuit, R.J.P. Corniu, C. Reyé, Synthesis, 1983, 294.