Furanose Synthesis via Regioselective Dihydroxylation of 1-Silyloxy-1,3-dienes: Application to the Furanose Unit of 4-epi-Hygromycin A

Synlett

Volumn , Issue 2, 2004, Pages 350-352

  Armstrong, Alan ^a   Gethin, David M ^b   Wheelhouse, Christopher J ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b ZOETIS   (United States)

Author keywords

Alkenes; Dihydroxylation; Osmium; Oxidations; Regioselective

Indexed keywords

ALCOHOL; ALKADIENE; ALKENE; HYGROMYCIN;

ARTICLE; DIHYDROXYLATION; EPIMERIZATION; OXIDATION; OXYGENATION; REACTION ANALYSIS; SYNTHESIS;

EID: 1242318584     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-44979     Document Type: Article

References (22)

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3. (a) Becker, H.; Soler, M. A.; Sharpless, K. B. Tetrahedron 1995, 51, 1345;
4. Other examples of regioselective AD of ester-substituted dienes include:. (b) Armstrong, R. W.; Tellew, J. E.; Moran, E. J. Tetrahedron Lett. 1996, 37, 447. (c) Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem.-Eur. J. 1995, 1, 467. (d) Bruckner, R.; Harcken, C. Tetrahedron Lett. 2001, 42, 3967. (e) For a recent example of synthesis of a xylulose derivative using regioselective AD of a 2-alkoxy-1,1-difluoro-1,3-diene, see: Cox, L. R.; DeBoos, G. A.; Fullbrook, J. J.; Percy, J. M.; Spencer, N. S.; Tolley, M. Org. Lett. 2003, 5, 337.
5. Other examples of regioselective AD of ester-substituted dienes include:. (b) Armstrong, R. W.; Tellew, J. E.; Moran, E. J. Tetrahedron Lett. 1996, 37, 447. (c) Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem.-Eur. J. 1995, 1, 467. (d) Bruckner, R.; Harcken, C. Tetrahedron Lett. 2001, 42, 3967. (e) For a recent example of synthesis of a xylulose derivative using regioselective AD of a 2-alkoxy-1,1-difluoro-1,3-diene, see: Cox, L. R.; DeBoos, G. A.; Fullbrook, J. J.; Percy, J. M.; Spencer, N. S.; Tolley, M. Org. Lett. 2003, 5, 337.
6. Other examples of regioselective AD of ester-substituted dienes include:. (b) Armstrong, R. W.; Tellew, J. E.; Moran, E. J. Tetrahedron Lett. 1996, 37, 447. (c) Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem.-Eur. J. 1995, 1, 467. (d) Bruckner, R.; Harcken, C. Tetrahedron Lett. 2001, 42, 3967. (e) For a recent example of synthesis of a xylulose derivative using regioselective AD of a 2-alkoxy-1,1-difluoro-1,3-diene, see: Cox, L. R.; DeBoos, G. A.; Fullbrook, J. J.; Percy, J. M.; Spencer, N. S.; Tolley, M. Org. Lett. 2003, 5, 337.
7. Other examples of regioselective AD of ester-substituted dienes include:. (b) Armstrong, R. W.; Tellew, J. E.; Moran, E. J. Tetrahedron Lett. 1996, 37, 447. (c) Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem.-Eur. J. 1995, 1, 467. (d) Bruckner, R.; Harcken, C. Tetrahedron Lett. 2001, 42, 3967. (e) For a recent example of synthesis of a xylulose derivative using regioselective AD of a 2-alkoxy-1,1-difluoro-1,3-diene, see: Cox, L. R.; DeBoos, G. A.; Fullbrook, J. J.; Percy, J. M.; Spencer, N. S.; Tolley, M. Org. Lett. 2003, 5, 337.
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13. 2. The absolute configuration of 9 is assigned based upon the Sharpless mnemonic. 1 The ee of (Z)-9 was determined using HPLC (Chiralcel OD, 1 mL per min, 5% IPA/hexane, detection at 210 nm, retention times: 11.8 min (minor enantiomer), 27.8 min (major enantiomer). We have been unable to determine the ee of (E)-9.
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15. 13C NMR resonances at δ = 201 and 200 ppm.
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21. H1 in the major anomer appeared as a singlet, while that in the minor was d, J = 3.6 Hz. Comparison to ref. 5a,b and to various pentafuranoses then suggests the anomeric configuration indicated. Stevens, J. D.; Fletcher, H. G. J. J. Org. Chem. 1968, 33, 1799.
22. + requires 484.2915. Found: 484.2919.