Inter- and intramolecular Diels-Alder cycloaddition of enantiopure 4,5-0, C-functionalized cyclohex-2-enone and its derivatives prepared from D-glucose 1

Journal of Carbohydrate Chemistry

Volumn 16, Issue 4-5, 1997, Pages 441-457

  Satake, Yuko ^a   Tadano, Kin Ichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BETULACEAE;

EID: 0039330010     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309708007327     Document Type: Article

References (19)

1. Presented at the XVIIIth International Carbohydrate Symposium, Milan, Italy, July 21-26, 1996.
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9. A similar phenomenon was reported previously: a) Y. K. Yur'ev, N. S. Zefirov, and A. A. Shteinman, Zh. Obshch. Khim., 33, 1150 (1963); CA, 59, 11395b (1963).
10. A similar phenomenon was reported previously: a) Y. K. Yur'ev, N. S. Zefirov, and A. A. Shteinman, Zh. Obshch. Khim., 33, 1150 (1963); CA, 59, 11395b (1963).
11. b) P. -Y. Renard and J.-Y. Lallemand, Synlett, 163 (1993) and references cited therein.
12. J. ApSimon, S. V. Seenu, M. R. L'Abbe and R. Seguin, Heterocycles, 15, 1079 (1981).
13. 2AlCl did not give any products.
14. 2, -15°C to rt, 3 h).
15. When each 5 or 6 was independently subjected to the thermal conditions (200 °C, 1 day), no interconversion was observed. These results indicated that thermal retroDiels-Alder process did not occur under the conditions used.
16. A. L. Gemal and J. L. Luche, J. Am. Chem. Soc., 103, 5454 (1981).
17. 4 in all respects.
18. Prolonging the reaction time for completion of the Diels-Alder cycloaddition of the subtrate 20 caused partial decomposition of 20, and the combined yield of 21-23 reduced significantly.
19. R. K. Boeckman, Jr. and D. M. Demko, J. Org. Chem., 47, 1789 (1982).