Stereo- and enantio-controlled synthesis of two naturally occurring polyoxygenated cyclohexenemethanols, (+)-epiepoxydon and (-)-phyllostine, via catalytic asymmetrization of a meso substrate

Tetrahedron Letters

Volumn 37, Issue 4, 1996, Pages 499-502

  Kamikubo, Takashi ^a   Hiroya, Kou ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE; EPIEPOXYDON; PHYLLOSTINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030033034     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02190-6     Document Type: Article

References (28)

1. Closse, A.; Mauli, R.; Sigg, H. P. Helv. Chim. Acta 1966, 49, 204.
2. Sakamura, S.; Niki, H.; Obata, Y.; Sakai, R.; Matsumoto, T. Agr. Biol. Chem. 1969, 33, 698.
3. Nagasawa, H.; Suzuki, A.; Tamura, S. Arg. Biol. Chem. 1978, 42, 1303.
4. Sekiguchi, J.; Gaucher, G. M. Biochem. J. 1979, 182, 445.
5. Sakamura, S.; Ito, J.; Sakai, R. Agr. Biol. Chem. 1970, 34, 153; 1971, 35, 105.
6. Sakamura, S.; Ito, J.; Sakai, R. Agr. Biol. Chem. 1970, 34, 153; 1971, 35, 105.
7. Racemic syntheses: a) Ichihara, A.; Oda, K.; Sakamura, S. Tetrahedron Lett. 1972, 5105.
8. b) Ichihara, A.; Kimura, R.; Oda, K.; Sakamura, S. Tetrahedron Lett. 1976, 4741.
9. c) Ichihara, A.; Kimura, R.; Oda, K.; Moriyasu, K.; Sakamura, S. Arg. Biol. Chem. 1982, 46, 1879.
10. Pertinent reviews, see: a) Ichihara, A. J. Syn. Org. Chem. Jpn. 1982, 40, 102.
11. b) Ichihara, A. Synthesis 1987, 207.
12. Ogasawara, K. Pure & Appl. Chem. 1994, 66, 2119.
13. Hiroya, K.; Kurihara, Y.; Ogasawara, K. Angew. Chem. Int. Ed. Engl. in press.
14. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932; Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245; Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
15. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932; Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245; Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
16. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932; Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245; Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
17. Kitamura, M.; Manabe, M.; Noyori, R.; Takaya, H. Tetrahedron Lett. 1987, 28, 4719. Pertinent reviews: Otsuka, S.; Tani, K. In Asymmetric Synthesis; Morrison, J. D. Ed.; Academic Press: New York, 1985; Vol. 5, 171; Noyori, R.; Kitamura, M. Modern Synthetic Methods, Schefford, R. Ed.; Springer: Heidelberg, 1989; Vol. 5, 115.; Otsuka, S.; Tani, K. Synthesis 1991, 665.
18. Kitamura, M.; Manabe, M.; Noyori, R.; Takaya, H. Tetrahedron Lett. 1987, 28, 4719. Pertinent reviews: Otsuka, S.; Tani, K. In Asymmetric Synthesis; Morrison, J. D. Ed.; Academic Press: New York, 1985; Vol. 5, 171; Noyori, R.; Kitamura, M. Modern Synthetic Methods, Schefford, R. Ed.; Springer: Heidelberg, 1989; Vol. 5, 115.; Otsuka, S.; Tani, K. Synthesis 1991, 665.
19. Kitamura, M.; Manabe, M.; Noyori, R.; Takaya, H. Tetrahedron Lett. 1987, 28, 4719. Pertinent reviews: Otsuka, S.; Tani, K. In Asymmetric Synthesis; Morrison, J. D. Ed.; Academic Press: New York, 1985; Vol. 5, 171; Noyori, R.; Kitamura, M. Modern Synthetic Methods, Schefford, R. Ed.; Springer: Heidelberg, 1989; Vol. 5, 115.; Otsuka, S.; Tani, K. Synthesis 1991, 665.
20. Kitamura, M.; Manabe, M.; Noyori, R.; Takaya, H. Tetrahedron Lett. 1987, 28, 4719. Pertinent reviews: Otsuka, S.; Tani, K. In Asymmetric Synthesis; Morrison, J. D. Ed.; Academic Press: New York, 1985; Vol. 5, 171; Noyori, R.; Kitamura, M. Modern Synthetic Methods, Schefford, R. Ed.; Springer: Heidelberg, 1989; Vol. 5, 115.; Otsuka, S.; Tani, K. Synthesis 1991, 665.
21. Ito, Y.; Hirano, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
22. Gemal, A. L.; Luche, J. L. J. Am. Chem. Soc. 1981, 103, 5454.
23. Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. Synthesis 1993, 948.
24. Kamikubo, T.; Ogasawara, K. Tetrahedron Lett. 1995, 36, 1685. In this report was described the transformation of the enzymatically prepared (+)-13 into 17 via 16.
25. a) Takano, S.; Moriya, M.; Ogasawara, K. Synlett 1993, 601.
26. b) Kamikubo, T.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1995, 1951.
27. Newton, R. F.; Reynolds, D. P.; Finch, M. A. W.; Kelly, D. R.; Roberts, S. M. Tetrahedron Lett. 1979, 3981.
28. 3): δ 2.03 (br s, 1H), 3.82-3.85 (m, 2H), 4.41 (dd, 1H, J=17.5 and 1.7 Hz), 4.59 (dd, 1H, J=17.5 and 1.9 Hz), 6.69 (dd, 1H, J=3.8 and 1.9 Hz).