Asymmetric synthesis of methyl bacteriopheophorbide-d and analogues by stereoselective reduction of the 3-acetyl to the 3-(1-hydroxyethyl) group

Tetrahedron Asymmetry

Volumn 9, Issue 12, 1998, Pages 2101-2111

  Tamiaki, Hitoshi ^b   Kouraba, Mitsuru ^b   Takeda, Kenji ^b   Kondo, Shin Ichi ^a,b   Tanikaga, Rikuhei ^b  

^a GUNMA UNIVERSITY   (Japan)

^b RITSUMEIKAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 ACETYL 13 OXO TETRAPYRROLE; BORANE DERIVATIVE; KETONE; METHYL BACTERIOPHEOPHORBIDE; OXAZABOROLIDINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; PHOTOSYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032546890     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00199-2     Document Type: Article

References (30)

1. Smith, K. M.; Goff, D. A. J. Chem. Soc., Perkin Trans. 1 1985, 1099-1113.
2. Holzwarth, A. R.; Griebenow, K.; Schaffner, K. J. Photochem. Photobiol. A: Chem. 1992, 65, 61-71; Bobe, F. W.; Pfenning, N.; Swanson, K. L.; Smith, K. M. Biochemistry 1990, 29, 4340-4348.
3. Holzwarth, A. R.; Griebenow, K.; Schaffner, K. J. Photochem. Photobiol. A: Chem. 1992, 65, 61-71; Bobe, F. W.; Pfenning, N.; Swanson, K. L.; Smith, K. M. Biochemistry 1990, 29, 4340-4348.
4. Tamiaki, H.; Takeuchi, S.; Tsudzuki, S.; Miyatake, T.; Tanikaga, R. Tetrahedron 1998, 54, in press.
5. Tamiaki, H.; Takeuchi, S.; Tanikaga, R.; Balaban, S. T.; Holzwarth, A. R.; Schaffner, K. Chem. Lett. 1994, 401-402;
6. Chiefari, J.; Griebenow, K.; Fages, F.; Griebenow, N.; Balaban, T. S.; Holzwarth, A. R.; Schaffner, K. J. Phys. Chem. 1995, 99, 1357-1365;
7. Balaban, T. S.; Holzwarth, A. R.; Schaffner, K. J. Mol. Str. 1995, 349, 183-186;
8. Balaban, T. S.; Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. J. Phys. Chem. B. 1997, 101, 3424-3431.
9. Smith, K. M.; Bisset, G. M. F.; Bushell, M. J. Org. Chem. 1980, 45, 2218-2224.
10. Tamiaki, H.; Watanabe, T.; Miyatake, T. J. Porphyrins Phthalocyanines 1998, 2, in press.
11. Salunkhe, A. M.; Burkhardt, E. R. Tetrahedron Lett. 1997, 38, 1523-1526.
12. Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553; Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7926.
13. Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553; Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7926.
14. Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784; Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475-1504: Singh, V. K. Synthesis 1992, 605-617.
15. Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784; Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475-1504: Singh, V. K. Synthesis 1992, 605-617.
16. Deloux, L.; Srebnik, M. Chem. Rev. 1993, 93, 763-784; Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475-1504: Singh, V. K. Synthesis 1992, 605-617.
17. Smith, J. R. L.; Calvin, M. J. Am. Chem. Soc. 1966, 88, 4500-4506.
18. Kusch, D.; Montforts, F.-P. Liebig Ann. 1996, 83-86; Kusch, D.; Montforts, F.-P. Tetrahedron: Asymmetry 1995, 6, 867-870; Kusch, D.; Töllner, E.; Lincke, A.; Montforts, F.-P. Angew. Chem. Int. Ed. Engl. 1995, 34, 784-787.
19. Kusch, D.; Montforts, F.-P. Liebig Ann. 1996, 83-86; Kusch, D.; Montforts, F.-P. Tetrahedron: Asymmetry 1995, 6, 867-870; Kusch, D.; Töllner, E.; Lincke, A.; Montforts, F.-P. Angew. Chem. Int. Ed. Engl. 1995, 34, 784-787.
20. Kusch, D.; Montforts, F.-P. Liebig Ann. 1996, 83-86; Kusch, D.; Montforts, F.-P. Tetrahedron: Asymmetry 1995, 6, 867-870; Kusch, D.; Töllner, E.; Lincke, A.; Montforts, F.-P. Angew. Chem. Int. Ed. Engl. 1995, 34, 784-787.
21. Prasad, K. P. K.; Joshi, N. N. Tetrahedron: Asymmetry 1996, 7, 3147-3152.
22. Brown, H. C.; Chandrasekharan, J.; Ramachandran, P. V. J. Am. Chem. Soc. 1988, 110, 1539-1546.
23. Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709-6716.
24. Sugi, K. D.; Nagata, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1996, 1081-1082.
25. Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531-5534.
26. Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299.
27. Ema, T. personal communication.
28. Tamiaki, H.; Kouraba, M. Tetrahedron 1997, 53, 10677-10688.
29. Tamiaki, H.; Miyatake, T.; Tanikaga, R. Tetrahedron Lett. 1997, 38, 267-270; Tamiaki, H.; Yagai, S.; Miyatake, T. in preparation.
30. Tamiaki, H.; Miyatake, T.; Tanikaga, R. Tetrahedron Lett. 1997, 38, 267-270; Tamiaki, H.; Yagai, S.; Miyatake, T. in preparation.