494
M.-A. N’Zoutani et al.
LETTER
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8
O
H
O
10
11
TIPSO
a)
b)
13
3
27
1
O
15
20
O
PMBO
OMe
28
8
(3) Iwasaki, S.; Kobayashi, H.; Furukawa, J.; Namikoshi, M.;
Okuda, S.; Sato, Z.; Matsuda, I.; Oda, T. J. Antibiot. 1984,
37, 354.
O
O
7
H
11
15
10
5
(4) (a) Tsuruo, T.; Oh-hara, T.; Iida, H.; Tsukagoshi, S.; Sato,
Z.; Matsuda, I.; Iwasaki, S.; Okuda, S.; Shimizu, F.;
Sasagawa, K.; Fukami, M.; Fukuda, K.; Arakawa, M.
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Y.; Ogawa, Y.; Imada, T.; Iwasaki, S.; Shimazaki, N.;
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Fiebig, H. H.; Fodstad, O.; Dreef-van der Meulen, H. C.;
Henrar, R. E. C.; Pinedo, H. M.; Schwartsmann, G. Ann.
Oncol. 1992, 3, 755.
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A.; Bissett, D.; Setanoians, A.; Hamilton, T.; Kerr, D. J.;
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(c) Bissett, D.; Graham, M. A.; Setanoians, A.; Chadwick,
G. A.; Wilson, P.; Koier, I.; Henrar, R.; Schwartsmann, G.;
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J. Br. J. Cancer 1996, 74, 1944.
HO
3
13
1
26
O
O
N
20
O
28
17
21
OMe
rhizoxin D 1b
Scheme 10 a) i) TASF, DMF, 0 °C, 12 h, 60%; ii) IBX, DMSO,
20 °C, 1 h, 95%; iii) (i-Pr)2NEt, LiCl, MeCN, 12 h, 50%; b) i) DDQ,
CH2Cl2, H2O, 20 °C, 2 h, 75%; ii) IBX, DMSO, 20 °C, 1 h, 90%; iii)
2, t-BuOK, DME, 0 °C, 30%; iv) HF·pyridine, THF 20 °C, 48 h, 55%.
Acknowledgment
We gratefully acknowledge the ‘Ligue Contre le Cancer’ for a
doctoral fellowship to Marie-Ange N’Zoutani. We also thank the
CNRS, UCP and ESCOM for financial support.
(7) Iwasaki, S.; Namikoshi, M.; Kobayashi, H.; Furukawa, J.;
Okuda, S. Chem. Pharm. Bull. 1986, 34, 1387.
(8) N’Zoutani, M.-A.; Pancrazi, A.; Ardisson, J. Synlett 2001,
769.
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