Synthesis of optically active analogs of α-tocopherol based on (S)-(+)-dihydromyrcene

Russian Chemical Bulletin

Volumn 49, Issue 9, 2000, Pages 1620-1623

  Odinokov, V N ^a   Spivak, A Yu ^a   Emel'yanova, G A ^a   Syutkina, E V ^a   Ushakova, Z I ^a   Khalilov, L M ^a  

^a INSTITUTE OF PETROCHEMISTRY AND CATALYSIS   (Russian Federation)

Author keywords

(3S) 3,7 dimethyloct 6 en 2 one; (3S) 3,7 dimethyloctan 2 one; (S) (+) 3,7 dimethylocta 1,6 diene ((S) (+) dihydromyrcene); Analogs of tocopherol (vitamin E); Isoprenoid vinyl alcohols

Indexed keywords

EID: 0034337338     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02495169     Document Type: Article

References (16)

1. K. Mukai, Y. Kageyama, T. Ishida, and K. Fukuda, J. Org. Chem., 1989, 54, 552; K. Mukai, K. Okabe, and H. Hosose, J. Org. Chem., 1989, 54, 557; B. C. Pearce, R. A. Parker, M. E. Deason, D. D. Dischino, E. Gillespie, A. A. Qureshi, K. Volk, and J. J. Kim Wright, J. Med. Chem., 1994, 37, 526; T. Rosenau and W. D. Habicker, Tetrahedron, 1995, 51, 7919; M. Kouma, T. Takagi, A. Ando, and I. Kumadaki, Chem. Pharm. Bull., 1995, 43, 1466; T. Rosenau, W. D. Habicker, and C. L. Chen, Heterocycles, 1996, 43, 787; T. Fujishima, H. Kagechika, and K. Shudo, Arch. Pharm., 1996, 329, 27; T. Rosenau and W. D. Habicker, Tetrahedron Lett., 1997, 38, 5959.
2. K. Mukai, Y. Kageyama, T. Ishida, and K. Fukuda, J. Org. Chem., 1989, 54, 552; K. Mukai, K. Okabe, and H. Hosose, J. Org. Chem., 1989, 54, 557; B. C. Pearce, R. A. Parker, M. E. Deason, D. D. Dischino, E. Gillespie, A. A. Qureshi, K. Volk, and J. J. Kim Wright, J. Med. Chem., 1994, 37, 526; T. Rosenau and W. D. Habicker, Tetrahedron, 1995, 51, 7919; M. Kouma, T. Takagi, A. Ando, and I. Kumadaki, Chem. Pharm. Bull., 1995, 43, 1466; T. Rosenau, W. D. Habicker, and C. L. Chen, Heterocycles, 1996, 43, 787; T. Fujishima, H. Kagechika, and K. Shudo, Arch. Pharm., 1996, 329, 27; T. Rosenau and W. D. Habicker, Tetrahedron Lett., 1997, 38, 5959.
3. K. Mukai, Y. Kageyama, T. Ishida, and K. Fukuda, J. Org. Chem., 1989, 54, 552; K. Mukai, K. Okabe, and H. Hosose, J. Org. Chem., 1989, 54, 557; B. C. Pearce, R. A. Parker, M. E. Deason, D. D. Dischino, E. Gillespie, A. A. Qureshi, K. Volk, and J. J. Kim Wright, J. Med. Chem., 1994, 37, 526; T. Rosenau and W. D. Habicker, Tetrahedron, 1995, 51, 7919; M. Kouma, T. Takagi, A. Ando, and I. Kumadaki, Chem. Pharm. Bull., 1995, 43, 1466; T. Rosenau, W. D. Habicker, and C. L. Chen, Heterocycles, 1996, 43, 787; T. Fujishima, H. Kagechika, and K. Shudo, Arch. Pharm., 1996, 329, 27; T. Rosenau and W. D. Habicker, Tetrahedron Lett., 1997, 38, 5959.
4. K. Mukai, Y. Kageyama, T. Ishida, and K. Fukuda, J. Org. Chem., 1989, 54, 552; K. Mukai, K. Okabe, and H. Hosose, J. Org. Chem., 1989, 54, 557; B. C. Pearce, R. A. Parker, M. E. Deason, D. D. Dischino, E. Gillespie, A. A. Qureshi, K. Volk, and J. J. Kim Wright, J. Med. Chem., 1994, 37, 526; T. Rosenau and W. D. Habicker, Tetrahedron, 1995, 51, 7919; M. Kouma, T. Takagi, A. Ando, and I. Kumadaki, Chem. Pharm. Bull., 1995, 43, 1466; T. Rosenau, W. D. Habicker, and C. L. Chen, Heterocycles, 1996, 43, 787; T. Fujishima, H. Kagechika, and K. Shudo, Arch. Pharm., 1996, 329, 27; T. Rosenau and W. D. Habicker, Tetrahedron Lett., 1997, 38, 5959.
5. K. Mukai, Y. Kageyama, T. Ishida, and K. Fukuda, J. Org. Chem., 1989, 54, 552; K. Mukai, K. Okabe, and H. Hosose, J. Org. Chem., 1989, 54, 557; B. C. Pearce, R. A. Parker, M. E. Deason, D. D. Dischino, E. Gillespie, A. A. Qureshi, K. Volk, and J. J. Kim Wright, J. Med. Chem., 1994, 37, 526; T. Rosenau and W. D. Habicker, Tetrahedron, 1995, 51, 7919; M. Kouma, T. Takagi, A. Ando, and I. Kumadaki, Chem. Pharm. Bull., 1995, 43, 1466; T. Rosenau, W. D. Habicker, and C. L. Chen, Heterocycles, 1996, 43, 787; T. Fujishima, H. Kagechika, and K. Shudo, Arch. Pharm., 1996, 329, 27; T. Rosenau and W. D. Habicker, Tetrahedron Lett., 1997, 38, 5959.
6. K. Mukai, Y. Kageyama, T. Ishida, and K. Fukuda, J. Org. Chem., 1989, 54, 552; K. Mukai, K. Okabe, and H. Hosose, J. Org. Chem., 1989, 54, 557; B. C. Pearce, R. A. Parker, M. E. Deason, D. D. Dischino, E. Gillespie, A. A. Qureshi, K. Volk, and J. J. Kim Wright, J. Med. Chem., 1994, 37, 526; T. Rosenau and W. D. Habicker, Tetrahedron, 1995, 51, 7919; M. Kouma, T. Takagi, A. Ando, and I. Kumadaki, Chem. Pharm. Bull., 1995, 43, 1466; T. Rosenau, W. D. Habicker, and C. L. Chen, Heterocycles, 1996, 43, 787; T. Fujishima, H. Kagechika, and K. Shudo, Arch. Pharm., 1996, 329, 27; T. Rosenau and W. D. Habicker, Tetrahedron Lett., 1997, 38, 5959.
7. K. Mukai, Y. Kageyama, T. Ishida, and K. Fukuda, J. Org. Chem., 1989, 54, 552; K. Mukai, K. Okabe, and H. Hosose, J. Org. Chem., 1989, 54, 557; B. C. Pearce, R. A. Parker, M. E. Deason, D. D. Dischino, E. Gillespie, A. A. Qureshi, K. Volk, and J. J. Kim Wright, J. Med. Chem., 1994, 37, 526; T. Rosenau and W. D. Habicker, Tetrahedron, 1995, 51, 7919; M. Kouma, T. Takagi, A. Ando, and I. Kumadaki, Chem. Pharm. Bull., 1995, 43, 1466; T. Rosenau, W. D. Habicker, and C. L. Chen, Heterocycles, 1996, 43, 787; T. Fujishima, H. Kagechika, and K. Shudo, Arch. Pharm., 1996, 329, 27; T. Rosenau and W. D. Habicker, Tetrahedron Lett., 1997, 38, 5959.
8. K. Mukai, Y. Kageyama, T. Ishida, and K. Fukuda, J. Org. Chem., 1989, 54, 552; K. Mukai, K. Okabe, and H. Hosose, J. Org. Chem., 1989, 54, 557; B. C. Pearce, R. A. Parker, M. E. Deason, D. D. Dischino, E. Gillespie, A. A. Qureshi, K. Volk, and J. J. Kim Wright, J. Med. Chem., 1994, 37, 526; T. Rosenau and W. D. Habicker, Tetrahedron, 1995, 51, 7919; M. Kouma, T. Takagi, A. Ando, and I. Kumadaki, Chem. Pharm. Bull., 1995, 43, 1466; T. Rosenau, W. D. Habicker, and C. L. Chen, Heterocycles, 1996, 43, 787; T. Fujishima, H. Kagechika, and K. Shudo, Arch. Pharm., 1996, 329, 27; T. Rosenau and W. D. Habicker, Tetrahedron Lett., 1997, 38, 5959.
9. E. I. Zakharova, K. A.-V. Shuaipov, V. V. Chudinova, S. M. Alekseev, and R. P. Evstigneeva, Bioorg. Khim. 1989, 15, 1268 [Sov. J. Bioorg. Chem., 1989, 15 (Engl. Transl.)]; K. I. Matveev, E. G. Zhizhina, and V. F. Odyakov, Khim. Prom. [Chem. Industry], 1996, 173 (in Russian).
10. E. I. Zakharova, K. A.-V. Shuaipov, V. V. Chudinova, S. M. Alekseev, and R. P. Evstigneeva, Bioorg. Khim. 1989, 15, 1268 [Sov. J. Bioorg. Chem., 1989, 15 (Engl. Transl.)]; K. I. Matveev, E. G. Zhizhina, and V. F. Odyakov, Khim. Prom. [Chem. Industry], 1996, 173 (in Russian).
11. E. I. Zakharova, K. A.-V. Shuaipov, V. V. Chudinova, S. M. Alekseev, and R. P. Evstigneeva, Bioorg. Khim. 1989, 15, 1268 [Sov. J. Bioorg. Chem., 1989, 15 (Engl. Transl.)]; K. I. Matveev, E. G. Zhizhina, and V. F. Odyakov, Khim. Prom. [Chem. Industry], 1996, 173 (in Russian).
12. G. Yu. Ishmuratov, M. P. Yakovleva, R. Ya. Kharisov, and G. A. Tolstikov, Usp. Khim., 1995, 66, 1095 [Russ. Chem. Rev., 1995, 66 (Engl. Transl.)].
13. G. Yu. Ishmuratov, M. P. Yakovleva, R. Ya. Kharisov, and G. A. Tolstikov, Usp. Khim., 1995, 66, 1095 [Russ. Chem. Rev., 1995, 66 (Engl. Transl.)].
14. V. N. Odinokov, G. Yu. Ishmuratov, I. M. Ladenkova, R. R. Muslukhov, A. A. Berg, E. P. Serebryakov, and G. A. Tolstikov, Khim. Prirod. Soedin., 1992, 117 [Chem. Nat. Comp., 1992 (Engl. Transl.)].
15. V. N. Odinokov, G. Yu. Ishmuratov, I. M. Ladenkova, R. R. Muslukhov, A. A. Berg, E. P. Serebryakov, and G. A. Tolstikov, Khim. Prirod. Soedin., 1992, 117 [Chem. Nat. Comp., 1992 (Engl. Transl.)].
16. S. Brownstein, G. W. Burton, L. Hughes, and K. U. Ingold, J. Org. Chem., 1989, 54, 560.