-
5
-
-
0024358482
-
-
(a) Aoyagi, T.; Yamamoto, T.; Kojiri, K.; Morishima, H.; Nagai, M.; Hamada, M.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1989, 42, 883.
-
(1989)
J. Antibiot.
, vol.42
, pp. 883
-
-
Aoyagi, T.1
Yamamoto, T.2
Kojiri, K.3
Morishima, H.4
Nagai, M.5
Hamada, M.6
Takeuchi, T.7
Umezawa, H.8
-
6
-
-
0024344288
-
-
mannostatin a
-
(b) Morishima, H.; Kojiri, K.; Yamamoto, T.; Aoyagi, T.; Nakamura, H.; Iitaka, Y. J. Antibiot. 1989, 42, 1008 (mannostatin a).
-
(1989)
J. Antibiot.
, vol.42
, pp. 1008
-
-
Morishima, H.1
Kojiri, K.2
Yamamoto, T.3
Aoyagi, T.4
Nakamura, H.5
Iitaka, Y.6
-
7
-
-
0026069785
-
-
trehazolin
-
(c) Ando, O.; Sataki, S.; Itoi, K.; Sato, A.; Nakajima, M.; Takahashi, S.; Haruyama, H. J. Antibiot. 1991, 44, 1165 (trehazolin).
-
(1991)
J. Antibiot.
, vol.44
, pp. 1165
-
-
Ando, O.1
Sataki, S.2
Itoi, K.3
Sato, A.4
Nakajima, M.5
Takahashi, S.6
Haruyama, H.7
-
8
-
-
0025607135
-
-
(a) Reviews: Suami, T.; Ogawa, S. Adv. Carbohydr. Chem. Biochem. 1990, 48, 21-90. Suami, T. Top. Curr. Chem. 1990, 154, 257- 283.
-
(1990)
Adv. Carbohydr. Chem. Biochem.
, vol.48
, pp. 21-90
-
-
Suami, T.1
Ogawa, S.2
-
9
-
-
0025607135
-
-
(a) Reviews: Suami, T.; Ogawa, S. Adv. Carbohydr. Chem. Biochem. 1990, 48, 21-90. Suami, T. Top. Curr. Chem. 1990, 154, 257- 283.
-
(1990)
Top. Curr. Chem.
, vol.154
, pp. 257-283
-
-
Suami, T.1
-
10
-
-
0025067472
-
-
(b) Atsumi, S.; Umezawa, K.; Iinuma, H.; Naganawa, H.; Nakamura, H.; Iitaka, Y.; Takeuchi, T. J. Antibiot. 1990, 43, 49.
-
(1990)
J. Antibiot.
, vol.43
, pp. 49
-
-
Atsumi, S.1
Umezawa, K.2
Iinuma, H.3
Naganawa, H.4
Nakamura, H.5
Iitaka, Y.6
Takeuchi, T.7
-
11
-
-
0022455206
-
-
(AO-128)
-
(c) Horii, S.; Fukase, H.; Kameda, Y.; Asano, N.; Matsui, K. J. Med. Chem. 1986, 29, 1038 (AO-128).
-
(1986)
J. Med. Chem.
, vol.29
, pp. 1038
-
-
Horii, S.1
Fukase, H.2
Kameda, Y.3
Asano, N.4
Matsui, K.5
-
12
-
-
0029065673
-
-
For recent references of six-membered ring derivatives see: (a) Jung, M. E.; Choe, S. W. T. J. Org. Chem. 1995, 60, 3280. (b) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 3280
-
-
Jung, M.E.1
Choe, S.W.T.2
-
13
-
-
0027989518
-
-
For recent references of six-membered ring derivatives see: (a) Jung, M. E.; Choe, S. W. T. J. Org. Chem. 1995, 60, 3280. (b) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 5099
-
-
Hudlicky, T.1
Rouden, J.2
Luna, H.3
Allen, S.4
-
14
-
-
0028351052
-
-
(a) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Org. Chem. 1994, 59, 813.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 813
-
-
Kobayashi, Y.1
Miyazaki, H.2
Shiozaki, M.3
-
15
-
-
0027933794
-
-
(b) Shiozaki, M.; Arai, M.; Kobayashi, Y.; Kasuya, A.; Miyamoto, S.; Furukawa, Y.; Takayama, T.; Haruyama, H. J. Org. Chem. 1994, 59, 4450.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 4450
-
-
Shiozaki, M.1
Arai, M.2
Kobayashi, Y.3
Kasuya, A.4
Miyamoto, S.5
Furukawa, Y.6
Takayama, T.7
Haruyama, H.8
-
16
-
-
0029000476
-
-
(c) Kobayashi, Y.; Shiozaki, M.; Ando, O. J. Org. Chem. 1995, 60, 2570.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 2570
-
-
Kobayashi, Y.1
Shiozaki, M.2
Ando, O.3
-
17
-
-
0028128999
-
-
(d) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 7461
-
-
Knapp, S.1
Purandare, A.2
Rupitz, K.3
Withers, S.G.4
-
18
-
-
0028841036
-
-
(e) Goering, B. K., Li, J.; Ganem, B. Tetrahedron Lett. 1995, 36, 8905.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 8905
-
-
Goering, B.K.1
Li, J.2
Ganem, B.3
-
26
-
-
0030058156
-
-
(h) Nishimura, Y.; Umezawa, Y.; Adachi, H.; Kondo, S.; Takeuchi, T. J. Org. Chem. 1996, 61, 480.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 480
-
-
Nishimura, Y.1
Umezawa, Y.2
Adachi, H.3
Kondo, S.4
Takeuchi, T.5
-
27
-
-
37049067456
-
-
(i) Ogawa, S.; Kimura, H.; Vehida, C.; Ohashi, T. J. Chem. Soc., Perkin Trans 1 1995, 1695.
-
(1995)
J. Chem. Soc., Perkin Trans
, vol.1
, pp. 1695
-
-
Ogawa, S.1
Kimura, H.2
Vehida, C.3
Ohashi, T.4
-
28
-
-
0028126847
-
-
(j) Ingall, A. H.; Moore, P. R.; Roberts, S. M. Tetrahedron: Asymmetry 1994, 5, 2155.
-
(1994)
Tetrahedron: Asymmetry
, vol.5
, pp. 2155
-
-
Ingall, A.H.1
Moore, P.R.2
Roberts, S.M.3
-
29
-
-
11944251609
-
-
For an overview of our work see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. (b) Solladié, G.; Carreño, M. C. In Organosulphur Chemistry: Synthetic Aspects; Page, B. C. P., Ed.; Academic Press: London, 1995; p 1.
-
(1995)
Chem. Rev.
, vol.95
, pp. 1717
-
-
Carreño, M.C.1
-
30
-
-
0004204930
-
-
Page, B. C. P., Ed.; Academic Press: London
-
For an overview of our work see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. (b) Solladié, G.; Carreño, M. C. In Organosulphur Chemistry: Synthetic Aspects; Page, B. C. P., Ed.; Academic Press: London, 1995; p 1.
-
(1995)
Organosulphur Chemistry: Synthetic Aspects
, pp. 1
-
-
Solladié, G.1
Carreño, M.C.2
-
31
-
-
0345431389
-
-
(a) Carreño, M. C.; García Ruano, J. L.; Rubio, A. Tetrahedron Lett. 1987, 28, 4861.
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 4861
-
-
Carreño, M.C.1
García Ruano, J.L.2
Rubio, A.3
-
32
-
-
0001296747
-
-
(b) Carreño, M. C.; García Ruano, J. L.; Martín, A. M.; Pedregal, C.; Rodríguez, J. H.; Rubio, A.; Sánchez, J.; Solladié, G. J. Org. Chem. 1990, 55, 2120.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 2120
-
-
Carreño, M.C.1
García Ruano, J.L.2
Martín, A.M.3
Pedregal, C.4
Rodríguez, J.H.5
Rubio, A.6
Sánchez, J.7
Solladié, G.8
-
33
-
-
0027982215
-
-
(c) Bueno, A. B.; Carreño, M. C.; García Ruano, J. L.; Peña, B.; Rubio, A.; Hoyos, M. A. Tetrahedron Lett. 1994, 50, 9355.
-
(1994)
Tetrahedron Lett.
, vol.50
, pp. 9355
-
-
Bueno, A.B.1
Carreño, M.C.2
García Ruano, J.L.3
Peña, B.4
Rubio, A.5
Hoyos, M.A.6
-
34
-
-
0025145386
-
-
(a) Solladié, G.; Rubio, A.; Carreño, M. C., García Ruano, J. L. Tetrahedron: Asymmetry 1990, 1, 187.
-
(1990)
Tetrahedron: Asymmetry
, vol.1
, pp. 187
-
-
Solladié, G.1
Rubio, A.2
Carreño, M.C.3
García Ruano, J.L.4
-
35
-
-
0000134888
-
-
(b) Solladié, G.; Maestro, M. C.; Rubio, A.; Pedregal, C.; Carreño, M. C.; García Ruano, J. L. J. Org. Chem. 1991, 56, 2317.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 2317
-
-
Solladié, G.1
Maestro, M.C.2
Rubio, A.3
Pedregal, C.4
Carreño, M.C.5
García Ruano, J.L.6
-
36
-
-
0025092295
-
-
Carreño, M. C.; García Ruano, J. L.; Garrido, M.; Ruiz, M. P.; Solladié, G. Tetrahedron Lett. 1990, 31, 6653.
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 6653
-
-
Carreño, M.C.1
García Ruano, J.L.2
Garrido, M.3
Ruiz, M.P.4
Solladié, G.5
-
38
-
-
37049081677
-
-
Carreño, M. C.; García Ruano, J. L.; Pedregal, C.; Rubio, A. J Chem. Soc., Perkin Trans. 1 1989, 1335.
-
(1989)
J Chem. Soc., Perkin Trans.
, vol.1
, pp. 1335
-
-
Carreño, M.C.1
García Ruano, J.L.2
Pedregal, C.3
Rubio, A.4
-
39
-
-
0000023224
-
-
With regard to the regioselectivity of cyclopentenone deprotonation (α′ or γ) see: Liang Chen, Y.; Mariano, P. S.; Little, G. M. O'Brian, D.; Huesmann, P. L. J. Org. Chem. 1981, 46, 4643. Koreeda M.; Mislankar, S. G. J. Am. Chem. Soc. 1983, 105, 7203.
-
(1981)
J. Org. Chem.
, vol.46
, pp. 4643
-
-
Liang Chen, Y.1
Mariano, P.S.2
Little, G.M.3
O'Brian, D.4
Huesmann, P.L.5
-
40
-
-
0010578048
-
-
With regard to the regioselectivity of cyclopentenone deprotonation (α′ or γ) see: Liang Chen, Y.; Mariano, P. S.; Little, G. M. O'Brian, D.; Huesmann, P. L. J. Org. Chem. 1981, 46, 4643. Koreeda M.; Mislankar, S. G. J. Am. Chem. Soc. 1983, 105, 7203.
-
(1983)
J. Am. Chem. Soc.
, vol.105
, pp. 7203
-
-
Koreeda, M.1
Mislankar, S.G.2
-
41
-
-
9344233092
-
-
Evans, D. A; Faul, M. M.; Colombo, J. J.; Basaha, J.; Clardy J.; Cherry, D. J. Am. Chem. Soc. 1992, 114, 5977.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 5977
-
-
Evans, D.A.1
Faul, M.M.2
Colombo, J.J.3
Basaha, J.4
Clardy, J.5
Cherry, D.6
-
42
-
-
0029055673
-
-
Enantiomer (R)-8 is also available using (+)-menthol as quiral auxiliary
-
García Ruano, J. L.; Alonso, R.; Zarzuelo, M. M.; Noheda, P. Tetrahedron: Asymmetry 1995, 6, 1133. Enantiomer (R)-8 is also available using (+)-menthol as quiral auxiliary.
-
(1995)
Tetrahedron: Asymmetry
, vol.6
, pp. 1133
-
-
García Ruano, J.L.1
Alonso, R.2
Zarzuelo, M.M.3
Noheda, P.4
-
43
-
-
8244230556
-
-
note
-
The absolute configuration of 9a and 9b was established by comparison of their NMR data with those of 2-sulfinylcyclopentanones previously described; see ref 8b.
-
-
-
-
44
-
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8244233890
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-
note
-
3 and confirmed in a further step by means of Mosher's esters of the hydroxy derivative 3.
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-
-
-
45
-
-
0026534428
-
-
(a) Barros, D.; Carreño, M. C.; García Ruano, J. L.; Maestro, M. C. Tetrahedron Lett. 1992, 33, 2733.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 2733
-
-
Barros, D.1
Carreño, M.C.2
García Ruano, J.L.3
Maestro, M.C.4
-
46
-
-
0027982215
-
-
(b) Bueno, A. B.; Carreño, M. C.; García Ruano, J. L.; Peña, B.; Rubio, A.; Hoyos, M. A. Tetrahedron 1994, 50, 9355.
-
(1994)
Tetrahedron
, vol.50
, pp. 9355
-
-
Bueno, A.B.1
Carreño, M.C.2
García Ruano, J.L.3
Peña, B.4
Rubio, A.5
Hoyos, M.A.6
-
47
-
-
8244252336
-
-
note
-
Chromatographic purification of the hydroxy sulfoxides 4 yielded 4-(p-tolylsulfinyl)-2-cyclopenten-1-one (12) (the corresponding thioether was derived from compound 10), as a result of the hydrolysis of the enol ether moiety and the dehydration of the carbinol. chemical equation presented.
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-
-
-
52
-
-
33947085552
-
-
See: (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512. (b) Yamaguchi, S. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 1, p 125. (c) Chan, T. H.; Nwe, K. T. J. Org. Chem. 1992, 57, 6107.
-
(1973)
J. Am. Chem. Soc.
, vol.95
, pp. 512
-
-
Dale, J.A.1
Mosher, H.S.2
-
53
-
-
33947085552
-
-
Morrison, J. D., Ed.; Academic Press: New York
-
See: (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512. (b) Yamaguchi, S. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 1, p 125. (c) Chan, T. H.; Nwe, K. T. J. Org. Chem. 1992, 57, 6107.
-
(1983)
Asymmetric Synthesis
, vol.1
, pp. 125
-
-
Yamaguchi, S.1
-
54
-
-
0000328533
-
-
See: (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512. (b) Yamaguchi, S. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 1, p 125. (c) Chan, T. H.; Nwe, K. T. J. Org. Chem. 1992, 57, 6107.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 6107
-
-
Chan, T.H.1
Nwe, K.T.2
-
55
-
-
8244231971
-
-
note
-
2 failed to yield the corresponding sulfinylcarbamate.
-
-
-
-
56
-
-
0001100617
-
-
(a) Hirama, M.; Hioki, H.; Itô, S. Tetrahedron Lett. 1988, 29, 3125.
-
(1988)
Tetrahedron Lett.
, vol.29
, pp. 3125
-
-
Hirama, M.1
Hioki, H.2
Itô, S.3
-
57
-
-
0028225136
-
-
(b) Bias, J. de: Carretero, J. C.; Domínguez, E. Tetrahedron Lett. 1994, 35, 4603.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 4603
-
-
De Bias, J.1
Carretero, J.C.2
Domínguez, E.3
-
58
-
-
8244226686
-
-
note
-
The use of the readily available (R)-8 (see ref 15) would give access to (R,R)-2, which possesses the same stereochemistry as mannostatin.
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