A New Methodology for Efficient Construction of 2,7-Dioxabicyclo[3.3.0]octane Derivatives

Synlett

Volumn 1997, Issue 4, 1997, Pages 387-389

  Ito, Katsuji ^a   Fukuda, Tsutomu ^b,c   Katsuki, Tsutomu ^b  

^a FUKUOKA UNIVERSITY OF EDUCATION   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

^c JAPAN SOCIETY FOR THE PROMOTION OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005536885     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-809     Document Type: Article

References (28)

1. Murakami, T.; Tanaka, N.; Kimura, T.; Noguchi, T.; Saiki, Y.; Chen, C. M. Chem. Pharm. Bull. 1984, 32, 1808.
2. Velasquez, S.; Jimeno, M. L.; Huss, S.; Balzarini, J.; Camarasa, M.-J. J. Org. Chem. 1994, 59, 7661.
3. Avenaciolide (3): a) Brookes, D.; Tidd, B. K.; Turner, W. B. J. Chem. Soc. 1963, 5385. b) Hughes, D. L. Acta Crystallogr. 1978, B34, 3674. 4-Epi-ethisolide (4): Krohn, K.; Ludewig, K.; Aust, H. J.; Draeger, S.; Schulz, B. J. Antibiot. 1994, 47, 113. Isoavenaciolide (5) and Ethisolide (6): Aldridge, D. C.; Turner, W. B. J. Chem. Soc. C 1971, 2431.
4. Avenaciolide (3): a) Brookes, D.; Tidd, B. K.; Turner, W. B. J. Chem. Soc. 1963, 5385. b) Hughes, D. L. Acta Crystallogr. 1978, B34, 3674. 4-Epi-ethisolide (4): Krohn, K.; Ludewig, K.; Aust, H. J.; Draeger, S.; Schulz, B. J. Antibiot. 1994, 47, 113. Isoavenaciolide (5) and Ethisolide (6): Aldridge, D. C.; Turner, W. B. J. Chem. Soc. C 1971, 2431.
5. Avenaciolide (3): a) Brookes, D.; Tidd, B. K.; Turner, W. B. J. Chem. Soc. 1963, 5385. b) Hughes, D. L. Acta Crystallogr. 1978, B34, 3674. 4-Epi-ethisolide (4): Krohn, K.; Ludewig, K.; Aust, H. J.; Draeger, S.; Schulz, B. J. Antibiot. 1994, 47, 113. Isoavenaciolide (5) and Ethisolide (6): Aldridge, D. C.; Turner, W. B. J. Chem. Soc. C 1971, 2431.
6. Avenaciolide (3): a) Brookes, D.; Tidd, B. K.; Turner, W. B. J. Chem. Soc. 1963, 5385. b) Hughes, D. L. Acta Crystallogr. 1978, B34, 3674. 4-Epi-ethisolide (4): Krohn, K.; Ludewig, K.; Aust, H. J.; Draeger, S.; Schulz, B. J. Antibiot. 1994, 47, 113. Isoavenaciolide (5) and Ethisolide (6): Aldridge, D. C.; Turner, W. B. J. Chem. Soc. C 1971, 2431.
7. a) Ito, K.; Yoshitake, M.; Katsuki, T. Heterocycles 1996, 42, 305.
8. b) Ito, K.; Yoshitake, M; Katsuki, T. Chem. Lett. 1995, 1027.
9. Ito, K.; Yoshitake, M.; Katsuki, T. Tetrahedron, 1996, 52, 3905.
10. Ito, K.; Katsuki, T. Chem. Lett. 1994, 1857.
11. a) Mulzer, J. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press, Oxford, 1991, Vol. 6; p 323; Bartlett, P. A. In Asymmetric Synthesis, Morrison, J. P., Ed.; Academic Press, Inc., Orlando, 1984, Vol. 3, p 411.
12. a) Mulzer, J. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press, Oxford, 1991, Vol. 6; p 323; Bartlett, P. A. In Asymmetric Synthesis, Morrison, J. P., Ed.; Academic Press, Inc., Orlando, 1984, Vol. 3, p 411.
13. Compound 13 was synthesized in a conventional manner from n-nonyne as follows: i) addition of n-nonyne to acrolein, ii) titanium-mediated kinetic resolution of the resulting racemic allylic alcohol, iii) protection of the hydroxyl group, iv) hydroboration and oxidation, v) tosylation of the resulting primary alcohol, vi) deprotection of THP ether, and vii) treatment of the resulting secondary alcohol with n-BuLi.
14. 3]. The minor enantiomers of recrystallized 9 and 8 were not detected by NMR analysis.
15. Brown, C. A.; Ahuja, V. K. J. Chem. Soc., Chem. Commun. 1973, 553.
16. Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143.
17. 7 gave the better yield. Burke, S. D.; Jung, K. W.; Perri, R. E. Tetrahedron Lett. 1994, 35, 5841.
18. Trömel, M.; Russ, M. Angew. Chem. Int. Ed. Engl. 1987, 26, 1007.
19. All the spectroscopic data of 7 and 8 are compatible with reported data (reference 15d).
20. Compound 7 was unstable and its specific rotation varied during the measurement. The value observed with freshly prepared sample was described in the text. This probably is a reason that the values of the reported specific rotations are different.
21. Barton, D. H. R.; Crich, D.; Lobberding, A.; Zard, S. Z. Tetrahedron 1986, 42, 2329.
22. The synthesis of 7 and 8 constitutes a formal total synthesis of (-)-avenaciolide and (-)-isoavenaciolide, respectively. a) Anderson. R. C.; Fraser-Reid, B. J. Am. Chem. Soc, 1975, 97, 3870. b) Anderson, R. C.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 4781. Suzuki, K.; Miyazawa, M.; Shimazaki, M.; Tsuchihashi, G. Tetrahedron Lett. 1986, 27, 6237. Suzuki, K.; Miyazawa, M.; Shimazaki, M.; Tsuchihashi, G. Tetrahedron 1988, 44, 4061. e) Burke, S. D.; Pacofsky, G. J.; Piscopio, A. D. J. Org. Chem. 1992, 57, 2228. f) Suginome, M.; Yamamoto, Y.; Fujii, K.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9608. g) Ohrui, H.; Emoto, S. Tetrahedron Lett. 1975, 42, 3657.
23. The synthesis of 7 and 8 constitutes a formal total synthesis of (-)-avenaciolide and (-)-isoavenaciolide, respectively. a) Anderson. R. C.; Fraser-Reid, B. J. Am. Chem. Soc, 1975, 97, 3870. b) Anderson, R. C.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 4781. Suzuki, K.; Miyazawa, M.; Shimazaki, M.; Tsuchihashi, G. Tetrahedron Lett. 1986, 27, 6237. Suzuki, K.; Miyazawa, M.; Shimazaki, M.; Tsuchihashi, G. Tetrahedron 1988, 44, 4061. e) Burke, S. D.; Pacofsky, G. J.; Piscopio, A. D. J. Org. Chem. 1992, 57, 2228. f) Suginome, M.; Yamamoto, Y.; Fujii, K.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9608. g) Ohrui, H.; Emoto, S. Tetrahedron Lett. 1975, 42, 3657.
24. The synthesis of 7 and 8 constitutes a formal total synthesis of (-)-avenaciolide and (-)-isoavenaciolide, respectively. a) Anderson. R. C.; Fraser-Reid, B. J. Am. Chem. Soc, 1975, 97, 3870. b) Anderson, R. C.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 4781. Suzuki, K.; Miyazawa, M.; Shimazaki, M.; Tsuchihashi, G. Tetrahedron Lett. 1986, 27, 6237. Suzuki, K.; Miyazawa, M.; Shimazaki, M.; Tsuchihashi, G. Tetrahedron 1988, 44, 4061. e) Burke, S. D.; Pacofsky, G. J.; Piscopio, A. D. J. Org. Chem. 1992, 57, 2228. f) Suginome, M.; Yamamoto, Y.; Fujii, K.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9608. g) Ohrui, H.; Emoto, S. Tetrahedron Lett. 1975, 42, 3657.
25. The synthesis of 7 and 8 constitutes a formal total synthesis of (-)-avenaciolide and (-)-isoavenaciolide, respectively. a) Anderson. R. C.; Fraser-Reid, B. J. Am. Chem. Soc, 1975, 97, 3870. b) Anderson, R. C.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 4781. Suzuki, K.; Miyazawa, M.; Shimazaki, M.; Tsuchihashi, G. Tetrahedron Lett. 1986, 27, 6237. Suzuki, K.; Miyazawa, M.; Shimazaki, M.; Tsuchihashi, G. Tetrahedron 1988, 44, 4061. e) Burke, S. D.; Pacofsky, G. J.; Piscopio, A. D. J. Org. Chem. 1992, 57, 2228. f) Suginome, M.; Yamamoto, Y.; Fujii, K.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9608. g) Ohrui, H.; Emoto, S. Tetrahedron Lett. 1975, 42, 3657.
26. The synthesis of 7 and 8 constitutes a formal total synthesis of (-)-avenaciolide and (-)-isoavenaciolide, respectively. a) Anderson. R. C.; Fraser-Reid, B. J. Am. Chem. Soc, 1975, 97, 3870. b) Anderson, R. C.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 4781. Suzuki, K.; Miyazawa, M.; Shimazaki, M.; Tsuchihashi, G. Tetrahedron Lett. 1986, 27, 6237. Suzuki, K.; Miyazawa, M.; Shimazaki, M.; Tsuchihashi, G. Tetrahedron 1988, 44, 4061. e) Burke, S. D.; Pacofsky, G. J.; Piscopio, A. D. J. Org. Chem. 1992, 57, 2228. f) Suginome, M.; Yamamoto, Y.; Fujii, K.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9608. g) Ohrui, H.; Emoto, S. Tetrahedron Lett. 1975, 42, 3657.
27. The synthesis of 7 and 8 constitutes a formal total synthesis of (-)-avenaciolide and (-)-isoavenaciolide, respectively. a) Anderson. R. C.; Fraser-Reid, B. J. Am. Chem. Soc, 1975, 97, 3870. b) Anderson, R. C.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 4781. Suzuki, K.; Miyazawa, M.; Shimazaki, M.; Tsuchihashi, G. Tetrahedron Lett. 1986, 27, 6237. Suzuki, K.; Miyazawa, M.; Shimazaki, M.; Tsuchihashi, G. Tetrahedron 1988, 44, 4061. e) Burke, S. D.; Pacofsky, G. J.; Piscopio, A. D. J. Org. Chem. 1992, 57, 2228. f) Suginome, M.; Yamamoto, Y.; Fujii, K.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9608. g) Ohrui, H.; Emoto, S. Tetrahedron Lett. 1975, 42, 3657.
28. The synthesis of 7 and 8 constitutes a formal total synthesis of (-)-avenaciolide and (-)-isoavenaciolide, respectively. a) Anderson. R. C.; Fraser-Reid, B. J. Am. Chem. Soc, 1975, 97, 3870. b) Anderson, R. C.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 4781. Suzuki, K.; Miyazawa, M.; Shimazaki, M.; Tsuchihashi, G. Tetrahedron Lett. 1986, 27, 6237. Suzuki, K.; Miyazawa, M.; Shimazaki, M.; Tsuchihashi, G. Tetrahedron 1988, 44, 4061. e) Burke, S. D.; Pacofsky, G. J.; Piscopio, A. D. J. Org. Chem. 1992, 57, 2228. f) Suginome, M.; Yamamoto, Y.; Fujii, K.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9608. g) Ohrui, H.; Emoto, S. Tetrahedron Lett. 1975, 42, 3657.