Synthetic Study on Lipid Part of Liposidomycins

Bulletin of the Korean Chemical Society

Volumn 18, Issue 5, 1997, Pages 465-467

  Kim, Kwan Soo ^a   Cheong, Chan Seong ^a   Hahn, Jung Suk ^a   Park II, Jong ^a  

^a Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001131775     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

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3. Kimura, K.; Miyata, N.; Kawanishi, G.; Kamio, Y.; Izaki, K.; Isono, K. Agric. Biol. Chem. 1989, 53, 1811-1815.
4. Ubukata, M.; Kimura, K.; Isono, K.; Nelson, C. C.; Gregson, J. M.; McCloskey, J. A. J. Org. Chem. 1992, 57, 6392-6403.
5. Kim, K. S.; Cho, I. H.; Ahn, Y. H.; Park, J. I. J. Chem. Soc., Perkin Trans, I 1995, 1783-1785.
6. Kim, K. S.; Ahn, Y. H.; Hurh, E. Y.; Kim, K. T.; Joo, Y. H. J. Bull. Korean Chem. Soc. 1994, 15, 829-831.
7. Kim, K. S.; Lim, J. W.; Joo, Y. H.; Kim, K. T.; Cho, I. H.; Ahn, Y. H. J. Carbohydr. Chem. 1995, 14, 439-443.
8. Kang, S. K.; Kim, W.; Moon, B. H. Synthesis 1985, 1161-1162.
9. (a) Tamura, M.; Kochi, J. Synthesis 1971, 303-305.
10. (b) Fouquent, G.; Schlosser, M. Angew. Chem. Int. Ed. Engl. 1974, 13, 82-83.
11. 3) δ 0.85 (d, J= 6.0 Hz, 6H), 1.0-2.0 (m, 23H), 3.2-4.0 (m, 4H), 4.5 (brs, 1H). All new compounds gave satisfactory spectroscopic and/or microanalytical data.
12. 3) δ 0.87 (d, J=6.7 Hz, 6H), 1.10-1.70 (m, 15H), 2.42 (m, 2H), 9.77 (t, J=1.7 Hz, 1H).
13. 3) δ 0.86 (d, J= 6.7 Hz, 6H), 1.10-1.65 (m, 20H), 2.34-2.56 (m, 2H), 2.93 (brs, 1H), 3.99 (m, 1H), 4.18 (q, J=7.1 Hz, 2H).
14. 3) δ 0.86 (d, J=6.6 Hz, 6H), 1.12-1.80 (m, 18H), 2.54 (m, 2H), 3.43 (s, 2H), 4.22 (q, J=7.0 Hz, 2H).
15. 3) δ 22.7, 25.5, 27.4, 28.0, 29.6, 29.9, 36.6, 39.1, 41.2, 51.7, 68.1, 173.5.
16. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129.
17. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
18. 3) δ 0.86 (d, J=6.6 Hz, 6H), 1.10-1.82 (m, 17H), 2.54-2.71 (m, 2H), 3.53 (s, 3H), 3.59 (s, 3H), 5.48 (m, 1H), 7.41 (m, 3H), 7.53 (m, 2H).
19. Prelog, V. Pure Appl. Chem. 1964, 9, 119-130.
20. D values in chloroform. For example, see: (a) Tulloch, A. P.; Spencer, J. F. T. Can. J. Chem. 1964, 42, 830-835. (b) Vesonder, R. F.; Wickerham, L. J.; Rohwedder, W. K. Can. J. Chem. 1968, 46, 2628-2629. (c) Nishikiori, T.; Nagasawa, H.; Muraoka, Y.; Aoyagi, T.; Umezawa, H. J. Antibiot. 1986, 39, 745-754. (d) Nakahata, M.; Imaida, M.; Ozaki, H.; Harada, T.; Tai, A. Bull. Chem. Soc. Jpn. 1982, 55, 2186-2189.
21. D values in chloroform. For example, see: (a) Tulloch, A. P.; Spencer, J. F. T. Can. J. Chem. 1964, 42, 830-835. (b) Vesonder, R. F.; Wickerham, L. J.; Rohwedder, W. K. Can. J. Chem. 1968, 46, 2628-2629. (c) Nishikiori, T.; Nagasawa, H.; Muraoka, Y.; Aoyagi, T.; Umezawa, H. J. Antibiot. 1986, 39, 745-754. (d) Nakahata, M.; Imaida, M.; Ozaki, H.; Harada, T.; Tai, A. Bull. Chem. Soc. Jpn. 1982, 55, 2186-2189.
22. D values in chloroform. For example, see: (a) Tulloch, A. P.; Spencer, J. F. T. Can. J. Chem. 1964, 42, 830-835. (b) Vesonder, R. F.; Wickerham, L. J.; Rohwedder, W. K. Can. J. Chem. 1968, 46, 2628-2629. (c) Nishikiori, T.; Nagasawa, H.; Muraoka, Y.; Aoyagi, T.; Umezawa, H. J. Antibiot. 1986, 39, 745-754. (d) Nakahata, M.; Imaida, M.; Ozaki, H.; Harada, T.; Tai, A. Bull. Chem. Soc. Jpn. 1982, 55, 2186-2189.
23. D values in chloroform. For example, see: (a) Tulloch, A. P.; Spencer, J. F. T. Can. J. Chem. 1964, 42, 830-835. (b) Vesonder, R. F.; Wickerham, L. J.; Rohwedder, W. K. Can. J. Chem. 1968, 46, 2628-2629. (c) Nishikiori, T.; Nagasawa, H.; Muraoka, Y.; Aoyagi, T.; Umezawa, H. J. Antibiot. 1986, 39, 745-754. (d) Nakahata, M.; Imaida, M.; Ozaki, H.; Harada, T.; Tai, A. Bull. Chem. Soc. Jpn. 1982, 55, 2186-2189.
24. Csuk, R.; Glanzer, B. I. Chem. Rev. 1991, 97, 49-97.
25. Wegrzynski, B.; Toome, V. Analytical Letters 1991, 24, 317-326.
26. Limstead, R. P.; Lunt, J. C.; Weedon, C. L. J. Chem. Soc. 1950, 3333-3335.
27. 3) δ 0.86 (d, J=6.6 Hz, 6H), 1.12-1.80 (m, 17H), 1.48 (s, 9H), 2.28-2.48 (m, 2H), 3.09 (brs, 1H), 3.96 (m, 1H). Acetylated t-butylester was also obtained as a side product but readily converted to compound 14 by hydrolysis with aqueous 1 M KOH.
28. +, 2), 387 (100), 370 (2), 355 (9), 255 (2), 227 (7), 161 (7), 143 (27).