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Yamaguchi, M.5
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12
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0342393708
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note
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The stereochemistry of the epoxy moiety of 3 was established by comparison of the proton chemical shifts due to the 8-H and 6-Me group from the same behavior observed between arenastatin A (1, 8-H: δ 3.68, 6-Me: δ 1.14) and the α-epoxy isomer of 1 (δ 3.59, 1.05). Namely, an obvious difference in chemical shifts of the 8-H and 6-Me groups was observed; the signals of 3 appeared in lower field (δ 3.69, 1.13) than those (δ 3.59, 1.04) of the α-isomer. This physicochemical property enabled us to establish stereochemistry on the 7, 8-epoxy moieties of the other analogs (4-6); 4: δ 3.67, 1.14, the α-epoxy isomer of 4: δ 3.59, 1.03, 5: δ 3.77, 1.11, the α-epoxy isomer of 5: δ 3.57, 1.05, 6: δ 3.68, 1.13, the α-epoxy isomer of 6: δ 3.58, 1.05.
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14
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0041537280
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Golakoti T., Ogino J., Heltzel C.E., Husebo T.L., Jenson C.M., Larsen L.K., Patterson G.M.L., Moore R.E., Mooberry S.L., Corbett T.H., Valeriote F.A. J. Am. Chem. Soc. 117:1995;12030-12049.
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Golakoti, T.1
Ogino, J.2
Heltzel, C.E.3
Husebo, T.L.4
Jenson, C.M.5
Larsen, L.K.6
Patterson, G.M.L.7
Moore, R.E.8
Mooberry, S.L.9
Corbett, T.H.10
Valeriote, F.A.11
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16
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0342828443
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note
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6-DMSO are listed. δ: 8.27 (1H, d, J=8.6 Hz, 15-NH), 8.21 (1H, d, J=7.9 Hz, 24-NH), 7.38-7.26 (5H, m, 10, 11, 12-H), 7.28 (1H, m, 22-NH), 7.10 (2H, d, J=8.6 Hz, 27-H), 6.80 (2H, d, J=8.6 Hz, 28-H), 6.36 (1H, ddd, J=4.3, 11.6, 15.3 Hz, 3-H), 5.75 (1H, d, J=15.3 Hz, 2-H), 5.10 (1H, brdd, J=5.5, 11.6 Hz, 5-H), 4.35 (1H, ddd, J=5.5, 8.6, 9.7 Hz, 15-H), 4.18 (1H, ddd, J=3.7, 7.9, 11.6 Hz, 24-H), 3.87 (1H, d, J=1.9 Hz, 8-H), 3.69 (3H, s, 29-OMe), 3.50 (1H, m, 22-Ha), 2.96 (3H, m, 7-H, 22-Hb, 25-Ha), 2.62 (2H, m, 4-Ha, 25-Hb), 2.24 (2H, m, 4-Hb, 21-Ha), 2.13 (1H, m, 21-Hb), 1.79 (1H, q-like, J=ca. 7 Hz, 6-H), 1.47 (1H, m, 17-H), 1.28 (1H, m, 16-Ha), 1.11 (1H, m, 16-Hb), 1.03 (3H, d, J=6.8 Hz, 13-H), 0.75, 0.74 (both 3H, d, J=6.7 Hz, 18, 19-H).
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