S. Ogawa, Y. Tezuka / Bioorg. Med. Chem. Lett. 16 (2006) 5238–5243
5243
21
9. (a) Takahashi, S.; Kinoshita, T.; Takahashi, M. J.
Antibiot. 1994, 47, 95; (b) Takahashi, M.; Tanzawa, K.;
Takahashi, S. J. Biol. Chem. 1994, 289, 369.
10. In this letter, the nomenclature of cyclitols follows
IUPAC-IUB 1973 Recommendations for Cyclitols [Pure.
Appl. Chem. 1974, 37, 285].
11. (a) Vieira de Almeida, M.; Dubreuil, D.; Cleophax, J.;
Verre-Sebrie, C.; Pipelier, M.; Prestat, G.; Vass, G.; Gero,
S. D. Tetrahedron 1999, 55, 7251, and references cited
therein; (b) Dubreuil, D.; Cleophax, J.; Vieira de Almeida,
M.; Pipelier, M.; Vass, G.; Gero, S. D. Tetrahedron 1999,
55, 7573, and references cited therein.
12. Safrany, S. T.; Wojcikiewicz, R. J. H.; Strupish, J.;
Nahorski, S. R.; Dubreuil, D.; Cleophax, J.; Gero, S.
D.; Potter, B. V. L. FEBS Lett. 1991, 278, 252.
13. Seewald, M. J.; Aksoy, I. A.; Powis, G.; Fauq, A. H.;
Kozikowski, A. P. J. Chem. Soc., Chem. Commun. 1990,
1638.
48 (in D2O); ½aꢂD +7.3 (c 2.5, H2O); d 4.53–4.29 (m, 1H,
H-5), 4.06–3.85 (m, 3H, H-1, H-2, H-4), 3.43 (dd, 1H,
J2,3 = 8.5 Hz, J3,4 = 8.8 Hz, H-3), 2.41–2.35 (m, 1H, H-
6eq), 1.75–1.65 (m, 1H, H-6ax). [MꢀH] m/z 405,
[M+Naꢀ2H] m/z 427, [Mꢀ2H]2 m/z 202; for compound
21
51 (in D2O); ½aꢂD +7.5 (c 1.4, H2O); d 4.90 (d, 1H,
J2,F = 48.6 Hz, H-2), 4.16–4.02 (m, 1H, H-4), 3.98–3.82
(m, 2H, H-1, H-5), 3.67 (dd, 1H, J1,6 = J5,6 = 9.5 Hz, H-
6), 2.41–2.30 (m, 1H, H-3eq), 1.60 (dddd, 1H,
J2,3ax = 2.2 Hz,
J3ax,4 = 12.9 Hz,
Jgem = 13.7 Hz,
J3ax,F = 46.9 Hz, H-3ax). [MꢀH] m/z 405, [M+Naꢀ2H]
23
m/z 427, [Mꢀ2H]2 m/z 202; for compound 59a (in
CDCl3); ½aꢂD +17 (c 2.4, CHCl3); d 7.34–7.01 (m, 40H,
8 · Ph), 5.08 and 4.44 (m, 18H, H-4, H-5, 8 · CH2Ph),
4.03–3.98 (m, 2H, 2 · H-20), 3.89 (dd, 1H, J3,4 = 9.4 Hz,
J2,3 = 9.8 Hz, H-3), 3.78 (br, 1H, H-1), 3.60–3.55 (m,
2H, 2 · H-10), 3.26 (dd, 1H, J1,2 = 2.7 Hz, J2,3 = 9.8 Hz,
H-2),
2.61
(ddd,
1H,
J1,6eq = J5,6eq = 4.4 Hz,
14. Kozikowski, A. P.; Ognyanov, V. I.; Fauq, A. H.;
Nahorski, S. R.; Wilcox, R. A. J. Am. Chem. Soc. 1993,
115, 4429.
Jgem = 13.9 Hz, H-6eq), 1.39–1.28 (m, 1H, H-6ax); and
26
for compound 59b (in CDCl3); ½aꢂD ꢀ129 (c 1.3,
CHCl3); d 7.36–7.01 (m, 40H, 8 · Ph), 5.08 and 4.56
(m, 17H, H-5, 8 · CH2Ph), 4.52 (dd, 1H, J4,5 = 9.0 Hz,
J3,4 = 9.3 Hz, H-4), 4.05–3.95 (m, 2H, 2 · H-30), 3.87
(dd, 1H, J3,4 = 9.3 Hz, J2,3 = 9.5 Hz, H-3), 3.76 (br, 1H,
H-1), 3.75–3.38 (m, 2H, 2 · H-10), 3.22 (dd, 1H,
J1,2 = 2.7 Hz, J2,3 = 9,5 Hz, H-2), 2.65 (ddd, 1H,
J1,6eq = J5,6eq = 4.4 Hz, Jgem = 14.4 Hz, H-6eq), 1.83–
1.79 (m, 2H, 2 · H-20), 1.39–1.30 (m, 1H, H-6ax).
15. 1H NMR (300 MHz) data for compound 32 (in D2O);
21
½aꢂD ꢀ19 (c 3.7, H2O); d 4.50–4.47 (m, 1H, H-2), 4.23–
4.12 (m, 1H, H-4), 3.90–3.81 (m, 2H, H-1, H-5), 3.70
(dd, 1H, J5,6 = 9.2 Hz, J1,6 = 9.6 Hz, H-6), 2.27 (ddd,
1H, J2,3eq = 4.4 Hz, J4,3eq = 4.7 Hz, Jgem = 14.4 Hz, H-
3eq), 1.52 (m, 1H, H-3ax). [MꢀH] m/z 482,
[M+Naꢀ2H] m/z 505, [Mꢀ2H]2 m/z 241; for compound