Electrophilic heteroatom cyclization of ω-alkenylphosphonic acid half esters giving cyclic phosphonates (phostones)

Heterocycles

Volumn 46, Issue 1, 1997, Pages 463-472

  Yokomatsu, Tsutomu ^a   Shioya, Yoshihito ^a   Iwasawa, Haruo ^a   Shibuya, Shiroshi ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001251715     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-s52     Document Type: Article

References (23)

1. For reviews on modified sugars: H. Paulsen, Angew. Chem., Int. Ed. Engl., 1966, 5, 495.
2. For recent synthesis of thia-sugars: M. Izumi, O. Tsuruta, and H. Hashimoto, Carbohydr. Res., 1996, 280, 287;
3. H. Hashimoto, M. Kawashima, and H. Yuasa, Carbohydr. Res., 1996, 282, 207.
4. For recent synthesis of aza-sugars: A. Baudat, S. Picasso, P. Vogel, Carbohydr. Res., 1996, 281, 277;
5. G. Gradnig, G. Legier, and A. E. Stütz, Carbohydr. Res., 1996, 287, 49.
6. For phostonc analogues of KDO: H. Molin, J.-O. Noren, and A. Claesson, Carbohydr, Res., 1989, 194, 209.
7. For phostone analogues of D-glucopyranosc and D-mannopyranose: J. W. Darrow and D. G. Dreuckhammer, J. Org. Chem., 1994, 59, 2976.
8. S. Hanessian, N. Galeotti, P. Rosen, G Olive, and S. Babu, Bioorg. Med. Chem. Lett., 1994, 4, 2763.
9. A. E. Wroblcwski, Liebigs Ann. Chem., 1986, 1448.
10. For reviews of elcctrophilic hctcroatom cyclization: G. Cardillo and M. Orena, Tetrahedron, 1990, 46, 3321;
11. K. E. Harding and T. H. Tiner, Electrophilic Heteroatom Cyclization. In Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 4, p. 363.
12. Y.-F. Zhao, S.-J. Yan, and C. Zhai, J. Org. Chem., 1985, 50, 2136.
13. Iodine-induced hetcroatom cyclization of dicthyl homoallylphosphate giving cyclic phosphate is known to work well: P. A. Bartlett, D. Richardoson, and J. Myerson, Tetrahedron, 1984, 40, 2317;
14. P. A. Bartlett and K. K. Jernstedt J. Am. Chem. Soc., 1977, 99, 4829.
15. For Pummerer rearrangement of selenoxides: J. A. Marshall and R. D. Royce, Jr., J. Org. Chem., 1982, 47, 693;
16. K. Haraguchi, S. Sato, H. Tanaka, and T. Miyasaka, Nucleosides and Nucleotides, 1992, 11, 483.
17. E. Kawashima, K. Toyama, K. Ohshima, M. Kainosho, Y. Kyogoku, and Y. Ishido, Tetrahedron Lett., 1995, 36, 6699.
18. Yield based on the recovered starting mesylate.
19. 2 produced from NBS in DMF.
20. 1H NMR analyses (NOE and 2D NOESY). However, the relative stereochemistry could not be determind by these analyses.
21. D. Goldsmith, D. Liotta, C. Lee, and G. Zima, Tetrahedron Lett., 1979, 4801;
22. D. L. Give, V. Farina, A. Singh, C. K. Wong, W. Kiel, and S. M. Menchen, J. Org. Chem., 1980, 45, 2120.
23. Triethylborane as a radical initiator: Y. Takeyama, Y. Ichinose, K. Oshima, and K. Utimoto, Tetrahedron Lett., 1989, 30, 3159.