A Convenient Synthesis of the (+) Enantiomer of Levoglucosenone and its 5-Hydroxymethyl Analog

Synlett

Volumn 1996, Issue 1, 1996, Pages 108-110

  Witczak, Zbigniew J ^a   Mielguj, Raphael ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542505535     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5326     Document Type: Article

References (27)

1. Presented in part during 207th ACS Meeting, March 13-18, 1994, San Diego, California, Abstract: CARB-99.
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6. e) Levoglucosenone and Levoglucosans Chemistry and Applications, Witczak, Z. J., Ed.; ATL Press Inc. Science Publishers, Mount Prospect, Illinois, 1994;
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15. Witczak, Z. J.; Li, Y. Tetrahedron Lett. 1995, 36, 2595 and references therein.
16. 2O): δ101.59 (C-1), 83.56 (C-5), 71.9 (C-2), 69.28 (C-3), 69.14 (C-4), 66.75 (C-6), 59.13 (C-7).
17. For alternative precursor with L-altro configuration see: Barilli, P.L.; Berti, G.; Catelani, G.; D'Andrea, F. Tetrahedron Lett. 1991, 32, 959.
18. Karl, H.; Lee, C.K.; Khan, R. Carbohydr.Res. 1982, 101, 31.
19. 3),
20. Davis, N. J.; Flitsch, S. L. Tetrahedron Lett. 1993, 34, 1181.
21. 3CO-).
22. 3).
23. 3), see: Matsumoto, K.; Ebata, T.; Koseki, K.; Kawakami, H.; Matsushita, H., Heterocycles 1991, 32, 2225.
24. D-530° (ref.2d) are also reported.
25. 3), 1.08 (s, 9H, t-Bu),
26. 3): δ 6.45 (d, 1H, H-3, J = 11Hz), 5.65 (d, 1H, H-4, J= 11Hz), 5.21 (s, 1H, H-1), 4.62 (d, 1H, H-7endo, J = 7.5Hz), 4.45 (q, 1H, H-7exo), 3.92 (dd, 1H, H-6exo, J = 7.5Hz ), 3.69 (ddd, 2H, H-6endo, J = 7.5Hz).
27. Witczak, Z. J.; Sun, J.; Mielguj, R. Bioorg. Med. Chem. Lett. 1995, 5, 2169.