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(a) For isolation of aspicilin see: Hesse, O. J. Prakt. Chem. 1900, 62, 430; 1904, 70, 449.
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(a) For isolation of aspicilin see: Hesse, O. J. Prakt. Chem. 1900, 62, 430; 1904, 70, 449.
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For X-ray structure determination see: Quinkert, G.; Heim, N.; Bats, J. W.; Oschkinat, H.; Kessler, H. Angew. Chem., Int. Ed. Eng. 1985, 24, 987.
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For synthesis of 1 from D-mannose, see: (a) Quinkert, G.; Fernholz, E.; Eckes, P.; Neumann, D.; Dürner, G. Helv. Chim. Acta 1989, 72, 1753.
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Eckes, P.3
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Dürner, G.5
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0023691114
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For synthesis of 1 from (S)-methyloxirane, see: (b) Quinkert, G.; Heim, N.; Glenneberg, J.; Döller, U.; Eichhorn, M.; Billhardt, U.-M.; Schwarz, C.; Zimmermann, G.; Bats, J. W.; Dürner, G. Helv. Chim. Acta 1988, 71, 1719. (c) Quinkert, G.; Becker, H.; Dürner, G. Tetrahedron Lett. 1991, 32, 7397. (d) Oppolzer, W.; Radinov, R. N.; De Brabander, J. Tetrahedron Lett. 1995, 36, 2607.
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Schwarz, C.7
Zimmermann, G.8
Bats, J.W.9
Dürner, G.10
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18
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0026317430
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For synthesis of 1 from (S)-methyloxirane, see: (b) Quinkert, G.; Heim, N.; Glenneberg, J.; Döller, U.; Eichhorn, M.; Billhardt, U.-M.; Schwarz, C.; Zimmermann, G.; Bats, J. W.; Dürner, G. Helv. Chim. Acta 1988, 71, 1719. (c) Quinkert, G.; Becker, H.; Dürner, G. Tetrahedron Lett. 1991, 32, 7397. (d) Oppolzer, W.; Radinov, R. N.; De Brabander, J. Tetrahedron Lett. 1995, 36, 2607.
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Quinkert, G.1
Becker, H.2
Dürner, G.3
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19
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0028924320
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For synthesis of 1 from (S)-methyloxirane, see: (b) Quinkert, G.; Heim, N.; Glenneberg, J.; Döller, U.; Eichhorn, M.; Billhardt, U.-M.; Schwarz, C.; Zimmermann, G.; Bats, J. W.; Dürner, G. Helv. Chim. Acta 1988, 71, 1719. (c) Quinkert, G.; Becker, H.; Dürner, G. Tetrahedron Lett. 1991, 32, 7397. (d) Oppolzer, W.; Radinov, R. N.; De Brabander, J. Tetrahedron Lett. 1995, 36, 2607.
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Radinov, R.N.2
De Brabander, J.3
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20
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0001177309
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For synthesis of (-)-aspicilin from (+)-diethyl L-tartrate and (R)-methyloxirane see: (e) Waanders, P. P.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1987, 28, 2409.
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0025771506
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For asymmetric synthesis of (-)-aspicilin utilizing a chiral sulfoxide group, see: (f) Solladié, G.; Fernandez, I.; Maestro, C. Tetrahedron: Asymmetry 1991, 2, 801. (g) For asymmetric synthesis of 1 via the SAMP/RAMP hydrazone technique, see: Enders, B.; Prokopenko, O. F. Liebigs Ann. 1995, 1185.
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Tetrahedron: Asymmetry
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Solladié, G.1
Fernandez, I.2
Maestro, C.3
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84988104072
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For asymmetric synthesis of (-)-aspicilin utilizing a chiral sulfoxide group, see: (f) Solladié, G.; Fernandez, I.; Maestro, C. Tetrahedron: Asymmetry 1991, 2, 801. (g) For asymmetric synthesis of 1 via the SAMP/RAMP hydrazone technique, see: Enders, B.; Prokopenko, O. F. Liebigs Ann. 1995, 1185.
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Liebigs Ann.
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28
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8044252872
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note
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Considering a simple case of a molecule containing only two asymmetric centers which have four possible stereoisomers: RR, RS, SS, and SR, the epimeric excess at one center is defined as: epe = ([RR] + [RS]) - ([SS] + [SR])/[RR] + [RS] + [SS] + [SR]
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30
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0001616071
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Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
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Keinan, E.; Seth, K. K.; Lamed, R.; Ghirlando, R.; Singh, S. P. Biocatalysis 1990, 3, 57.
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Keinan, E.1
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Ghirlando, R.4
Singh, S.P.5
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33
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8044248472
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In comparison, the Quinkert synthesis of (+)-aspicilin from D-mannose (reference 12a) was achieved in 13% overall yield
-
In comparison, the Quinkert synthesis of (+)-aspicilin from D-mannose (reference 12a) was achieved in 13% overall yield.
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