Convenient synthesis of (3S,5S)-5-hydroxy- and (3R,5S)-5-chloropiperazic acids of a peptide antibiotic, monamycin G3

Chemistry Letters

Volumn , Issue 11, 2001, Pages 1172-1173

  Ushiyama, Reiko ^a   Yonezawa, Yasuchika ^a   Shin, Chung Gi ^a  

^a KANAGAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035541224     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.1172     Document Type: Article

References (16)

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3. c) C. Hassall, R. Morton, Y. Ogihara, and D. Phillips, J. Chem. Soc. C, 1971, 526;
4. d) C. Hassall, W. Thomas, and M. Moschidis, J. Chem. Soc., Perkin I, 1977, 2369.
5. K. Hale, N. Jogiya, and S. Manaviazar, Tetrahedron Lett., 39, 1763 (1998).
6. T. Kamenecka and S. Danishefsky, Angew. Chem. Int. Ed., 37, 2995 (1998).
7. K. Depew, T. Kamenecka, and S. Danishefsky, Tetrahedron Lett., 41, 289 (2000).
8. Y. Nakamura and C. Shin, Chem. Lett.. 1991, 1953.
9. M. Taniguchi, K. Koga, and S. Yamada, Tetrahedron, 30, 3547 (1974).
10. 3) δ = 1.07(s, 9H, TPS's t-Bu), 1.46 and 1.47(each s, 18H, Boc × 2), 2.45-2.62 (m, 2H, H-4), 3.65 and 3.87 (each dd, 2H, H-6, J = 3.0, 11.5 Hz), 4.58 (d, 1H, H-5, J = 8.5 Hz), 5.14 (br s, 1H, H-3), 6.50 (br s, 1H, NH), 7.34-7.44 and 7.59-7.70 (each m, 10H, TPS's Ph × 2).
11. 6) δ = 1.52 (s, 18H, Boc × 2), 1.99 (s, 3H, Ac), 2.03-2.14 (m, 1H, H-4 ax), 2.40 (dd, 1H, H-4 eq, J= 1.4, 14.6 Hz), 3.08-3.10 (m, 1H, H-6 ax), 3.76 (s, 3H, Me), 4.19 (br d, 1H, H-6 eq, J = 13.8 Hz), 4.89 (br s, 1H, H-5), 4.96 (d, 1H, H-3, J = 6.8 Hz).
12. 6) δ = 1.32 and 1.39 (each s, 18H, Boc × 2), 1.81 (s, 3H, Ac), 1.99 (ddd, 1H, H-4 eq, J = 3.0, 6.5, 14.8 Hz), 2.26 (br d, 1H, H-4 ax, J = 14.5 Hz), 2.91 and 3.05 (each d, 1H, H6 ax, J = each 14.5 Hz), 3.60 (s, 3H, OMe), 3.97-4.05 (m, 1H, H-6 eq), 4.67-4.85 (m, 2H, H-3 and H-5).
13. 1H NMR δ = 2.14 (s, 3H, Ac), 2.26 (d, 1H, H-4 ax, J = 12.4 Hz), 2.46-2.54 (m, 1H, H4 eq), 3.16(dd, 1H, H-6 eq, J= 3.2, 13.5 Hz), 3.83 (d, 1H, H-6 eq, J = 13.2 Hz), 5.00 (t, 1H, H-5, J = 4.3 Hz), 5.20 (d, 1H, H-3, J = 3.5 Hz), 7.55 (d, 1H, DNP's Ph-6, J = 9.7 Hz), 8.34 (dd, 1H, DNP's Ph5,7 = 2.7, 9.7 Hz), 8.77 (d, 1H, DNP's Ph-4, J = 2.7 Hz).
14. 6) δ = 1.40 and 1.45 (each s, 18H, Boc × 2), 1.89 (ddd, 1H, H-4 ax, J = 5.9, 10.7, 13.8 Hz), 2.44 (br s, 1H, H-4 eq), 2.88 (dd, 1H, H-6 ax, J = 9.9, 12.6 Hz), 3.68 (s, 3H, OMe), 4.31 (ddd, 1H, H-6 eq, J = 3.5, 5.7, 10.3 Hz), 4.41 (dt, 1H, H-5, J = 5.7, 10.3 Hz), 5.00 (dd, 1H, H-3, J = 2.7, 5.9 Hz).
15. A. Kozikowski and J. Lee, Tetrahedron. Lett., 29, 3053 (1988).
16. 6) δ = 1.39 and 1.44 (each s, 18H, Boc × 2), 1.88 (ddd, 1H, H-4 ax, J = 6.0, 11.0, 13.5 Hz), 2.44 (br d, 1H, H-4 eq, J = 13. 5Hz), 2.87 (t, 1H, H-6 ax, J = 11.0 Hz), 3.67 (s, 3H, OMe), 4.30 (dd, 1H, H-6 eq, 7 = 4.5, 12.8 Hz), 4.40 (ddd, 1H, H-5, 7 = 4.5, 11.0, 15.4 Hz), 4.99 (d, 1H, H-3, J= 3.5 Hz).