A new chiral route to optically pure 3-oxodicyclopentadiene: A versatile chiral cyclopentadienone synthon, via contra-steric Diels-Alder reaction

Synthesis

Volumn , Issue 9, 1996, Pages 1101-1108

  Sugahara, Tsutomu ^a   Kuroyanagi, Yukari ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

chiral cyclopentadienone synthon; chiral synthon; contra steric Diels Alder reaction; lipase mediated kinetic transesterification; meso trick; oxodicyclopentadiene; symmetrization

Indexed keywords

CYCLOPENTADIENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029810491     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4342     Document Type: Article

References (26)

1. For pertinent reviews see: (a) Ogasawara, K. Pure & Appl. Chem. 1994, 66, 2119. (b) Ogasawara, K. J. Synth. Org. Chem. Jpn. 1996, 54, 15.
2. For pertinent reviews see: (a) Ogasawara, K. Pure & Appl. Chem. 1994, 66, 2119. (b) Ogasawara, K. J. Synth. Org. Chem. Jpn. 1996, 54, 15.
3. Synthesis of optically active KDP (1): (a) Woodward, R. B.; Katz, T. T. Tetrahedron 1959, 5, 79. (b) Ito, T.; Okamoto, Y.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1985, 55, 3631. (c) Klunder, A. J. H.; Huisinga, W. B.; Hulshof, A.; Zwanenburg, B. Tetrahedron Lett. 1986, 27, 2543 and 1987, 28, 359. (d) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271. (e) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1989, 359. (f) Takano, S.; Inomata, K.; Takahashi, M.; Ogasawara, K. Synlett 1991, 636. (g) Garland, R. B.; Miyano, M.; Prireh, D.; Clare, M.; Finnegan, P. M.; Swenton, L. J. Org. Chem. 1990, 55, 5854. (h) Childs, B. J.; Edwards, G. L. Tetrahedron Lett. 1993, 34, 5341. (i) Sato, M.; Hattori, H.; Murakami, M.; Kaneko, C. Chem. Lett. 1993, 1919. (j) Liu, Z.-Y.; He,L.; Zheng, H. Tetrahedron: Asymmetry 1993, 4, 2277. (k) Tanaka, K.; Ogasawara, K. Synthesis 1995, 1237.
4. Synthesis of optically active KDP (1): (a) Woodward, R. B.; Katz, T. T. Tetrahedron 1959, 5, 79. (b) Ito, T.; Okamoto, Y.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1985, 55, 3631. (c) Klunder, A. J. H.; Huisinga, W. B.; Hulshof, A.; Zwanenburg, B. Tetrahedron Lett. 1986, 27, 2543 and 1987, 28, 359. (d) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271. (e) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1989, 359. (f) Takano, S.; Inomata, K.; Takahashi, M.; Ogasawara, K. Synlett 1991, 636. (g) Garland, R. B.; Miyano, M.; Prireh, D.; Clare, M.; Finnegan, P. M.; Swenton, L. J. Org. Chem. 1990, 55, 5854. (h) Childs, B. J.; Edwards, G. L. Tetrahedron Lett. 1993, 34, 5341. (i) Sato, M.; Hattori, H.; Murakami, M.; Kaneko, C. Chem. Lett. 1993, 1919. (j) Liu, Z.-Y.; He,L.; Zheng, H. Tetrahedron: Asymmetry 1993, 4, 2277. (k) Tanaka, K.; Ogasawara, K. Synthesis 1995, 1237.
5. Synthesis of optically active KDP (1): (a) Woodward, R. B.; Katz, T. T. Tetrahedron 1959, 5, 79. (b) Ito, T.; Okamoto, Y.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1985, 55, 3631. (c) Klunder, A. J. H.; Huisinga, W. B.; Hulshof, A.; Zwanenburg, B. Tetrahedron Lett. 1986, 27, 2543 and 1987, 28, 359. (d) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271. (e) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1989, 359. (f) Takano, S.; Inomata, K.; Takahashi, M.; Ogasawara, K. Synlett 1991, 636. (g) Garland, R. B.; Miyano, M.; Prireh, D.; Clare, M.; Finnegan, P. M.; Swenton, L. J. Org. Chem. 1990, 55, 5854. (h) Childs, B. J.; Edwards, G. L. Tetrahedron Lett. 1993, 34, 5341. (i) Sato, M.; Hattori, H.; Murakami, M.; Kaneko, C. Chem. Lett. 1993, 1919. (j) Liu, Z.-Y.; He,L.; Zheng, H. Tetrahedron: Asymmetry 1993, 4, 2277. (k) Tanaka, K.; Ogasawara, K. Synthesis 1995, 1237.
6. Synthesis of optically active KDP (1): (a) Woodward, R. B.; Katz, T. T. Tetrahedron 1959, 5, 79. (b) Ito, T.; Okamoto, Y.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1985, 55, 3631. (c) Klunder, A. J. H.; Huisinga, W. B.; Hulshof, A.; Zwanenburg, B. Tetrahedron Lett. 1986, 27, 2543 and 1987, 28, 359. (d) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271. (e) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1989, 359. (f) Takano, S.; Inomata, K.; Takahashi, M.; Ogasawara, K. Synlett 1991, 636. (g) Garland, R. B.; Miyano, M.; Prireh, D.; Clare, M.; Finnegan, P. M.; Swenton, L. J. Org. Chem. 1990, 55, 5854. (h) Childs, B. J.; Edwards, G. L. Tetrahedron Lett. 1993, 34, 5341. (i) Sato, M.; Hattori, H.; Murakami, M.; Kaneko, C. Chem. Lett. 1993, 1919. (j) Liu, Z.-Y.; He,L.; Zheng, H. Tetrahedron: Asymmetry 1993, 4, 2277. (k) Tanaka, K.; Ogasawara, K. Synthesis 1995, 1237.
7. Synthesis of optically active KDP (1): (a) Woodward, R. B.; Katz, T. T. Tetrahedron 1959, 5, 79. (b) Ito, T.; Okamoto, Y.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1985, 55, 3631. (c) Klunder, A. J. H.; Huisinga, W. B.; Hulshof, A.; Zwanenburg, B. Tetrahedron Lett. 1986, 27, 2543 and 1987, 28, 359. (d) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271. (e) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1989, 359. (f) Takano, S.; Inomata, K.; Takahashi, M.; Ogasawara, K. Synlett 1991, 636. (g) Garland, R. B.; Miyano, M.; Prireh, D.; Clare, M.; Finnegan, P. M.; Swenton, L. J. Org. Chem. 1990, 55, 5854. (h) Childs, B. J.; Edwards, G. L. Tetrahedron Lett. 1993, 34, 5341. (i) Sato, M.; Hattori, H.; Murakami, M.; Kaneko, C. Chem. Lett. 1993, 1919. (j) Liu, Z.-Y.; He,L.; Zheng, H. Tetrahedron: Asymmetry 1993, 4, 2277. (k) Tanaka, K.; Ogasawara, K. Synthesis 1995, 1237.
8. Synthesis of optically active KDP (1): (a) Woodward, R. B.; Katz, T. T. Tetrahedron 1959, 5, 79. (b) Ito, T.; Okamoto, Y.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1985, 55, 3631. (c) Klunder, A. J. H.; Huisinga, W. B.; Hulshof, A.; Zwanenburg, B. Tetrahedron Lett. 1986, 27, 2543 and 1987, 28, 359. (d) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271. (e) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1989, 359. (f) Takano, S.; Inomata, K.; Takahashi, M.; Ogasawara, K. Synlett 1991, 636. (g) Garland, R. B.; Miyano, M.; Prireh, D.; Clare, M.; Finnegan, P. M.; Swenton, L. J. Org. Chem. 1990, 55, 5854. (h) Childs, B. J.; Edwards, G. L. Tetrahedron Lett. 1993, 34, 5341. (i) Sato, M.; Hattori, H.; Murakami, M.; Kaneko, C. Chem. Lett. 1993, 1919. (j) Liu, Z.-Y.; He,L.; Zheng, H. Tetrahedron: Asymmetry 1993, 4, 2277. (k) Tanaka, K.; Ogasawara, K. Synthesis 1995, 1237.
9. Synthesis of optically active KDP (1): (a) Woodward, R. B.; Katz, T. T. Tetrahedron 1959, 5, 79. (b) Ito, T.; Okamoto, Y.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1985, 55, 3631. (c) Klunder, A. J. H.; Huisinga, W. B.; Hulshof, A.; Zwanenburg, B. Tetrahedron Lett. 1986, 27, 2543 and 1987, 28, 359. (d) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271. (e) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1989, 359. (f) Takano, S.; Inomata, K.; Takahashi, M.; Ogasawara, K. Synlett 1991, 636. (g) Garland, R. B.; Miyano, M.; Prireh, D.; Clare, M.; Finnegan, P. M.; Swenton, L. J. Org. Chem. 1990, 55, 5854. (h) Childs, B. J.; Edwards, G. L. Tetrahedron Lett. 1993, 34, 5341. (i) Sato, M.; Hattori, H.; Murakami, M.; Kaneko, C. Chem. Lett. 1993, 1919. (j) Liu, Z.-Y.; He,L.; Zheng, H. Tetrahedron: Asymmetry 1993, 4, 2277. (k) Tanaka, K.; Ogasawara, K. Synthesis 1995, 1237.
10. Synthesis of optically active KDP (1): (a) Woodward, R. B.; Katz, T. T. Tetrahedron 1959, 5, 79. (b) Ito, T.; Okamoto, Y.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1985, 55, 3631. (c) Klunder, A. J. H.; Huisinga, W. B.; Hulshof, A.; Zwanenburg, B. Tetrahedron Lett. 1986, 27, 2543 and 1987, 28, 359. (d) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271. (e) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1989, 359. (f) Takano, S.; Inomata, K.; Takahashi, M.; Ogasawara, K. Synlett 1991, 636. (g) Garland, R. B.; Miyano, M.; Prireh, D.; Clare, M.; Finnegan, P. M.; Swenton, L. J. Org. Chem. 1990, 55, 5854. (h) Childs, B. J.; Edwards, G. L. Tetrahedron Lett. 1993, 34, 5341. (i) Sato, M.; Hattori, H.; Murakami, M.; Kaneko, C. Chem. Lett. 1993, 1919. (j) Liu, Z.-Y.; He,L.; Zheng, H. Tetrahedron: Asymmetry 1993, 4, 2277. (k) Tanaka, K.; Ogasawara, K. Synthesis 1995, 1237.
11. Synthesis of optically active KDP (1): (a) Woodward, R. B.; Katz, T. T. Tetrahedron 1959, 5, 79. (b) Ito, T.; Okamoto, Y.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1985, 55, 3631. (c) Klunder, A. J. H.; Huisinga, W. B.; Hulshof, A.; Zwanenburg, B. Tetrahedron Lett. 1986, 27, 2543 and 1987, 28, 359. (d) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271. (e) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1989, 359. (f) Takano, S.; Inomata, K.; Takahashi, M.; Ogasawara, K. Synlett 1991, 636. (g) Garland, R. B.; Miyano, M.; Prireh, D.; Clare, M.; Finnegan, P. M.; Swenton, L. J. Org. Chem. 1990, 55, 5854. (h) Childs, B. J.; Edwards, G. L. Tetrahedron Lett. 1993, 34, 5341. (i) Sato, M.; Hattori, H.; Murakami, M.; Kaneko, C. Chem. Lett. 1993, 1919. (j) Liu, Z.-Y.; He,L.; Zheng, H. Tetrahedron: Asymmetry 1993, 4, 2277. (k) Tanaka, K.; Ogasawara, K. Synthesis 1995, 1237.
12. Synthesis of optically active KDP (1): (a) Woodward, R. B.; Katz, T. T. Tetrahedron 1959, 5, 79. (b) Ito, T.; Okamoto, Y.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1985, 55, 3631. (c) Klunder, A. J. H.; Huisinga, W. B.; Hulshof, A.; Zwanenburg, B. Tetrahedron Lett. 1986, 27, 2543 and 1987, 28, 359. (d) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271. (e) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1989, 359. (f) Takano, S.; Inomata, K.; Takahashi, M.; Ogasawara, K. Synlett 1991, 636. (g) Garland, R. B.; Miyano, M.; Prireh, D.; Clare, M.; Finnegan, P. M.; Swenton, L. J. Org. Chem. 1990, 55, 5854. (h) Childs, B. J.; Edwards, G. L. Tetrahedron Lett. 1993, 34, 5341. (i) Sato, M.; Hattori, H.; Murakami, M.; Kaneko, C. Chem. Lett. 1993, 1919. (j) Liu, Z.-Y.; He,L.; Zheng, H. Tetrahedron: Asymmetry 1993, 4, 2277. (k) Tanaka, K.; Ogasawara, K. Synthesis 1995, 1237.
13. Synthesis of optically active KDP (1): (a) Woodward, R. B.; Katz, T. T. Tetrahedron 1959, 5, 79. (b) Ito, T.; Okamoto, Y.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1985, 55, 3631. (c) Klunder, A. J. H.; Huisinga, W. B.; Hulshof, A.; Zwanenburg, B. Tetrahedron Lett. 1986, 27, 2543 and 1987, 28, 359. (d) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271. (e) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1989, 359. (f) Takano, S.; Inomata, K.; Takahashi, M.; Ogasawara, K. Synlett 1991, 636. (g) Garland, R. B.; Miyano, M.; Prireh, D.; Clare, M.; Finnegan, P. M.; Swenton, L. J. Org. Chem. 1990, 55, 5854. (h) Childs, B. J.; Edwards, G. L. Tetrahedron Lett. 1993, 34, 5341. (i) Sato, M.; Hattori, H.; Murakami, M.; Kaneko, C. Chem. Lett. 1993, 1919. (j) Liu, Z.-Y.; He,L.; Zheng, H. Tetrahedron: Asymmetry 1993, 4, 2277. (k) Tanaka, K.; Ogasawara, K. Synthesis 1995, 1237.
14. Synthesis of optically active KDP (1): (a) Woodward, R. B.; Katz, T. T. Tetrahedron 1959, 5, 79. (b) Ito, T.; Okamoto, Y.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1985, 55, 3631. (c) Klunder, A. J. H.; Huisinga, W. B.; Hulshof, A.; Zwanenburg, B. Tetrahedron Lett. 1986, 27, 2543 and 1987, 28, 359. (d) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271. (e) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1989, 359. (f) Takano, S.; Inomata, K.; Takahashi, M.; Ogasawara, K. Synlett 1991, 636. (g) Garland, R. B.; Miyano, M.; Prireh, D.; Clare, M.; Finnegan, P. M.; Swenton, L. J. Org. Chem. 1990, 55, 5854. (h) Childs, B. J.; Edwards, G. L. Tetrahedron Lett. 1993, 34, 5341. (i) Sato, M.; Hattori, H.; Murakami, M.; Kaneko, C. Chem. Lett. 1993, 1919. (j) Liu, Z.-Y.; He,L.; Zheng, H. Tetrahedron: Asymmetry 1993, 4, 2277. (k) Tanaka, K.; Ogasawara, K. Synthesis 1995, 1237.
15. Takano, S.; Kasahara, C.; Ogasawara, K. Heterocycles 1981, 16, 605.
16. For a pertinent monograph, see: Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994.
17. Haubenstock, H.; Mennitt, P. G.; Butler, P. E. J. Org. Chem. 1970, 35, 3208.
18. Gemal, A. L.; Luche, T. L. J. Am. Chem. Soc. 1981, 103, 5454.
19. Chen, Z.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 371.
20. Schlessinger, R. H.; Nugent, R. A. J. Am. Chem. Soc. 1982, 104, 1116.
21. Dols, P. P. M. A.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron 1994, 50, 8515.
22. A part of the present work was reported as a preliminary form: Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1996, 37, 205.
23. cf. Coxon, J. M.; McDonald, D. Q. Tetrahedron Lett. 1992, 33, 651 and references cited therein.
24. We thank Mr. Shinji Tarama, Toyobo Co. Ltd., for a donation of lipase LIP.
25. Parikh, J. R.; Doering, W. v. E. J. Am. Chem. Soc. 1967, 89, 5505.
26. Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. Synthesis 1993, 948.