-
2
-
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0026498676
-
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Hall, C.C.1
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3
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0032488918
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Nielsen, J.7
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5
-
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33744806798
-
-
Ph.D. Dissertation, Eidgenossischen Technischen Hochschule, Zurich
-
Vasella, A. T. Ph.D. Dissertation, Eidgenossischen Technischen Hochschule, Zurich, 1972.
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Vasella, A.T.1
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6
-
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0037330943
-
-
It has recently become apparent that several sordaricin derivatives exhibit antifungal activities, see: Quesnelle, C. A.; Gill, P.; Dodier, M.; Laurent, D. S.; Serrano-Wu, M.; Marinier, A.; Martel, A.; Mazzucco, C. E.; Stickle, T. M.; Barrett, J. F.; Vyas, D. M.; Balasubramanian, B. N. Bioorg. Med. Chem. Lett. 2003, 13, 519-524.
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Quesnelle, C.A.1
Gill, P.2
Dodier, M.3
Laurent, D.S.4
Serrano-Wu, M.5
Marinier, A.6
Martel, A.7
Mazzucco, C.E.8
Stickle, T.M.9
Barrett, J.F.10
Vyas, D.M.11
Balasubramanian, B.N.12
-
7
-
-
33744808733
-
-
note
-
The numbers on each carbon atom of intermediates 8, 13, 14, 18, 19, 20, 21, 33, and 34 correspond to those of sordaricin (2).
-
-
-
-
10
-
-
0027279913
-
-
Kato, N.; Kusakabe, S.; Wu, X.; Kamitamari, M.; Takeshita, H. J. Chem. Soc., Chem. Commun. 1993, 1002-1004.
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Kato, N.1
Kusakabe, S.2
Wu, X.3
Kamitamari, M.4
Takeshita, H.5
-
11
-
-
33744800178
-
-
Ph.D. Dissertation, ETH, Zurich, Switzerland
-
Borschberg, H. J. Ph.D. Dissertation, ETH, Zurich, Switzerland, 1975.
-
(1975)
-
-
Borschberg, H.J.1
-
12
-
-
0041810236
-
-
For a review of the biogenetic intramolecular [4+2]-cycloaddition, see: (a) Stocking, E. M.; Williams, R. M. Angew. Chem., Int. Ed. 2003, 42, 3078-3115.
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Angew. Chem., Int. Ed.
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Stocking, E.M.1
Williams, R.M.2
-
13
-
-
0036259981
-
-
(b) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698.
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Nicolaou, K.C.1
Snyder, S.A.2
Montagnon, T.3
Vassilikogiannakis, G.4
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14
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4644362453
-
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Kitamura, M.; Chiba, S.; Narasaka, K. Chem. Lett. 2004, 33, 942-943.
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Chem. Lett.
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Kitamura, M.1
Chiba, S.2
Narasaka, K.3
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16
-
-
0346602829
-
-
(b) Tsuji, J. Tetrahedron 1986, 42, 4361-4401.
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(1986)
Tetrahedron
, vol.42
, pp. 4361-4401
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Tsuji, J.1
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18
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33645123653
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Chiba, S.; Cao, Z.; El Bialy, S. A. A.; Narasaka, K. Chem. Lett. 2006, 35, 18-19.
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Chiba, S.1
Cao, Z.2
El Bialy, S.A.A.3
Narasaka, K.4
-
19
-
-
0035925012
-
-
Barros, M. T.; Maycock, C. D.; Ventura, M. R. J. Chem. Soc., Perkin Trans. 1 2001, 166-173.
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Barros, M.T.1
Maycock, C.D.2
Ventura, M.R.3
-
20
-
-
0001432697
-
-
Matsuzawa, S.; Horiguchi, Y.; Nakamura, E.; Kuwajima, I. Tetrahedron 1989, 45, 349-362.
-
(1989)
Tetrahedron
, vol.45
, pp. 349-362
-
-
Matsuzawa, S.1
Horiguchi, Y.2
Nakamura, E.3
Kuwajima, I.4
-
22
-
-
0032891037
-
-
Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Ikeno, T.; Narasaka, K. Bull. Chem. Soc. Jpn. 1999, 72, 85-97.
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-
-
Iwasawa, N.1
Funahashi, M.2
Hayakawa, S.3
Ikeno, T.4
Narasaka, K.5
-
26
-
-
33744826443
-
-
note
-
2O, cat. DMAp→pyridine, rt, 2 h 95%
-
-
-
-
27
-
-
33744818366
-
-
CCDC-295066 contains the supplementary crystallographic data for compound 5. These data can be obtained free of charge via www. ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB21 EZ, U.K.; fax (+44)1223-336-033; or deposit@cdc.cam.ac.uk) .
-
-
-
-
28
-
-
33744800702
-
-
note
-
Synthetic schemes of the substrate 24 were depicted in the Supporting Information.
-
-
-
-
29
-
-
0037083881
-
-
There are some reports on the transition-metal catalyzed construction of bicyclo[2.2.1]heptan-2-one derivatives, see: (a) Langer, P.; Holtz, E.; Saleh, N. N. R. Chem.-Eur. J. 2002, 8, 917-928.
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Chem.-Eur. J.
, vol.8
, pp. 917-928
-
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Langer, P.1
Holtz, E.2
Saleh, N.N.R.3
-
31
-
-
13444306280
-
-
Miura, T.; Sasaki, T.; Nakazawa, H.; Murakami, M. J. Am. Chem. Soc. 2005, 127, 1390-1391.
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, vol.127
, pp. 1390-1391
-
-
Miura, T.1
Sasaki, T.2
Nakazawa, H.3
Murakami, M.4
-
32
-
-
33744802117
-
-
note
-
This approach was carried out on racemic 5.
-
-
-
-
34
-
-
0001553502
-
-
Lipshutz, B. H.; Koerner, M.; Parker, D. A. Tetrahedron Lett. 1987, 28, 945-948.
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Tetrahedron Lett.
, vol.28
, pp. 945-948
-
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Lipshutz, B.H.1
Koerner, M.2
Parker, D.A.3
-
35
-
-
0000488020
-
-
Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158-163.
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-
Hayashi, T.1
Konishi, M.2
Kobori, Y.3
Kumada, M.4
Higuchi, T.5
Hirotsu, K.6
-
36
-
-
26844522419
-
-
Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392-4398.
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Imamoto, T.1
Takiyama, N.2
Nakamura, K.3
Hatajima, T.4
Kamiya, Y.5
-
37
-
-
33744790792
-
-
note
-
In the absence of HMPA, the desired 29 was obtained only in 58% yield along with 35% yield of the hydride adduct 30.
-
-
-
-
41
-
-
0343777362
-
-
Nicolaou, K. C.; Rodriguez, R. M.; Mitchell, H. J.; Suzuki, H.; Flyaktakidou, K. C.; Baudoin, O.; van Delft, F. L. Chem.-Eur. J. 2000, 6, 3095-3115.
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, vol.6
, pp. 3095-3115
-
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Nicolaou, K.C.1
Rodriguez, R.M.2
Mitchell, H.J.3
Suzuki, H.4
Flyaktakidou, K.C.5
Baudoin, O.6
Van Delft, F.L.7
-
42
-
-
33744797267
-
-
David, S.; Thieffry, A.; Veyrieres, A. J. Chem. Soc., Perkin Trans. 1 1981, 1976-1801.
-
(1981)
J. Chem. Soc., Perkin Trans. 1
, pp. 1976-11801
-
-
David, S.1
Thieffry, A.2
Veyrieres, A.3
-
43
-
-
33744826716
-
-
note
-
The hydride attack occurred from the opposite side of the bulky thiophenyl group at C-I, which occupies an axial position (shown below). The configuration of 42 was readily assigned by inspection of the 1,2-coupling constant.
-
-
-
-
44
-
-
0030506198
-
-
There are some reports on the synthesis of β-2-deoxyribonucleosides using the 1,3-anchimeric assistance, see: (a) Mukaiyama, T.; Uchiro, H.; Hirano, N.; Ichikawa, T. Chem. Lett. 1996, 629-630.
-
(1996)
Chem. Lett.
, pp. 629-630
-
-
Mukaiyama, T.1
Uchiro, H.2
Hirano, N.3
Ichikawa, T.4
-
45
-
-
0030532975
-
-
(b) Mukaiama, T.; Hirano, N.; Nishida, M.; Uchiro, H. Chem. Lett. 1996, 99-100.
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(1996)
Chem. Lett.
, pp. 99-100
-
-
Mukaiama, T.1
Hirano, N.2
Nishida, M.3
Uchiro, H.4
-
46
-
-
0028126452
-
-
Young, R. J.; Shaw-Ponter, S.; Hardy, G. W.; Mills, G. Tetrahedron Lett. 1994, 35, 8687-8690.
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(1994)
Tetrahedron Lett.
, vol.35
, pp. 8687-8690
-
-
Young, R.J.1
Shaw-Ponter, S.2
Hardy, G.W.3
Mills, G.4
-
48
-
-
0000851520
-
-
(e) Ichikawa, Y.; Kubota, H.; Fujita, K.; Okauchi, T.; Narasaka, K. Bull. Chem. Soc. Jpn. 1989, 62, 845-852.
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Ichikawa, Y.1
Kubota, H.2
Fujita, K.3
Okauchi, T.4
Narasaka, K.5
-
49
-
-
0021997784
-
-
Wiesner et al. reported the synthesis of β-2-deoxyglycosides by the anchimeric assistance of a N-methylurethane group and a 4-methoxybenzoyl group, see: Wiesner, K.; Tsai, T. Y. R.; Jin, H. Helv. Chim. Acta 1985. 68, 300-314.
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(1985)
Chim. Acta
, vol.68
, pp. 300-314
-
-
Wiesner, K.1
Tsai, T.Y.R.2
Helv, J.H.3
-
50
-
-
84972955605
-
-
However, Binkley et al. suggested that the anchimeric assistance from the C-3 position was not the dominating characteristic of glycosyl donors having an acyloxy group at the C-2 position, see: Binkley, R. W.; Koholic, D. J. J. Carbohydr. Chem. 1988, 7, 487-489.
-
(1988)
J. Carbohydr. Chem.
, vol.7
, pp. 487-489
-
-
Binkley, R.W.1
Koholic, D.J.2
-
52
-
-
33744819078
-
-
note
-
2O, α-47b was preferentially obtained in 46% yield with 1:3 (β:α) selectivity.
-
-
-
-
53
-
-
33744811878
-
-
note
-
Interestingly, in the case of trichloroimidate 4b′ as a glycosyl donor, α-selective glycosidation proceeded to give 46b in 80% yield with 1:20 (β:α) selectivity.
-
-
-
-
54
-
-
33744787782
-
-
note
-
Synthetic sordarin was tested for fungal growth inhibition in C. albicans, C. glabrata, C. parapsilosis, and C. neoformans.
-
-
-
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