Contra-steric Diels-Alder route to 3-oxodicyclopentadiene and meso 3,5-endo-dihydroxy-4,5-dihydrodicyclopentadiene

Tetrahedron Letters

Volumn 37, Issue 2, 1996, Pages 205-208

  Sugahara, Tsutomu ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTADIENE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

BETULACEAE;

EID: 0030070995     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02129-9     Document Type: Article

References (23)

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2. Preparation of optically active 3-oxodicyclopentadiene (1), see: (a) Woodward, R. B.; Katz, T. J. Tetrahedron 1959, 5, 70;
3. (b) Ito, T.; Okamoto, Y.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1985, 58, 3631;
4. (c) Klunder, A. J. H.; Huizinga, W. B.; Hulshof, A. J. M.; Zwanenburg, B. Z. Tetrahedron Lett. 1986, 27, 2543: 1987, 28, 357;
5. (c) Klunder, A. J. H.; Huizinga, W. B.; Hulshof, A. J. M.; Zwanenburg, B. Z. Tetrahedron Lett. 1986, 27, 2543: 1987, 28, 357;
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11. (i) Liu, Z. -Y.; He, L.; Zheng, H. Tetrahedron: Asymmetry 1993, 4, 2277;
12. (j) Childs, B. J.; Edwards, G. L. Tetrahedron Lett. 1993, 34, 5341.
13. For a pertinent review, see: (a) Ogasawara, K. Pure & Appl. Chem. 1994, 66, 2119;
14. (b) Ogasawara, K. J. Syn. Org. Chem. Jpn. in press.
15. Takano, S.; Kasahara, C.; Ogasawara, K. Heterocycles 1981, 16, 605.
16. Haubenstock, H.; Mennitt, P. G.; Butler, P. E. J. Org. Chem. 1970, 35, 3208.
17. Chen, Z.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 371.
18. Schlessinger, R. H.; Nugent, R. A. J. Am. Chem. Soc. 1982, 104, 1116.
19. We are indebted Dr. Keita Matsumoto, Taisho Pharmaceutical Co., for carrying out X ray analysis.
20. Coxon, J. M.; McDonald, D. Q. Tetrahedron Lett. 1992, 33, 651 and references cited therein.
21. Dols, P. P. M. A.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1994, 50, 8515.
22. Cf. Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. Synthesis 1993, 948.
23. We thank Mr. Shinji Tarama, Toyobo Co., Osaka, Japan, for a donation of lipase LIP.