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0344870148
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11c,12,17
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0345301406
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note
-
2O, bis(1,1-dimethylethyl) dicarbonate; BOP, (1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; BOP-Cl, N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride; CSA, 10-camphorsulfonic acid; DBU, 1,8-diazabicyclo[5.4.0]undec-7-ene; DCC, dicyclohexylcarbodiimide; DEAD, diethyl azodicarboxylate; DMAP, 4-(dimethylamino)pyridine; DPPA, diphenylphosphoryl azide; EDC, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride; FDPP, pentafluorophenyl diphenylphosphinate; HOBt, 1-hydroxybenzotriazole; TFA, trifluoroacetic acid.
-
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52
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0344870146
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note
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23
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54
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84912953797
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0344438322
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note
-
2O gave 14 of 80% ee as determined by optical rotation. That 80% ee is the minimum enantiopurity of 5 is further supported by obtention of (Z)-15 and (E)-15 in >90% combined yield; other diastereomers were not detected.
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61
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0001852179
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1H NMR in analogy with related compounds: (a) Arenal, I.; Bernabe, M.; Fernadez-Alvarez, E. An. Quim., Ser. C 1981, 77, 56-62.
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0010580051
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1H NMR on the basis of the well-documented trend that the chemical shifts for the vinyl proton, the vinyl methyl group, and the enamine N-H are at lower fields in the (E)-isomers than in the (Z)-isomers. For example, see: (a) Srinivasan, A.; Richards, K. D.; Olsen, R. K. Tetrahedron Lett. 1976, 891-894.
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84985180861
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Isomerization during acylation with C-terminal α,β-unsaturated amino acids is precedented: Makowski, M.; Rzezotarska, B.; Kubica, Z.; Pietrzynski, G.; Hetper, J. Liebigs Ann. Chem. 1986, 980-991.
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85082557998
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(b) Schmidt, U.; Utz, R.; Lieberknecht, A.; Griesser, H.; Potzolli, B.; Bahr, J.; Wagner, K.; Fischer, P. Synthesis 1987, 236-241.
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0345301401
-
-
note
-
C < 0.5).
-
-
-
-
80
-
-
0344870143
-
-
note
-
Retention times for 1 and 2 were 30.4 and 29.8 min, respectively, with a hypersil ODS column (5-μm particle size; 4.6 × 200 mm) using MeCN/water gradient elution (1 mL/min; 25-75% MeCN over 35 min).
-
-
-
-
81
-
-
0344007028
-
-
note
-
2; benzene/ ether/acetone, 90:5:5) of a 10:1 mixture of (Z)-15 and (E)-15.
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0001289004
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(a) Mazur, R. H.; Pilipauskas, D. R. Pept.: Synth, Struct., Funct., Proc. Am. Pept. Symp., 7th; Rich, D. H.; Gross, E., Eds.; Pierce Chem. Co.: Rockford, IL, 1981; pp 81-84.
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86
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For other examples of dehydroamino acid syntheses by selenoxide fragmentation, see: (a) Walter, R.; Roy, J. J. Org. Chem. 1971, 36, 2561-6563.
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Roy, J.2
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(b) Reich, H. J.; Jasperse, C. P.; Renga, J. M. J. Org. Chem. 1986, 51, 2981-2988.
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(c) Hashimoto, K.; Sakai, M.; Okuno, T.; Shirahama, H. Chem. Commun. 1996, 1139-1140.
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Hashimoto, K.1
Sakai, M.2
Okuno, T.3
Shirahama, H.4
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89
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0344870140
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-
note
-
Phomalide and isophomalide are separable (PTLC; 30% ethyl acetate in hexane, multiple development), albeit with considerable difficulty (phomalide is slightly less polar) and with low efficiency (i.e., mainly mixed fractions are obtained).
-
-
-
-
90
-
-
0345301400
-
-
note
-
Obtained in 90% yield from 10 and (2R)-2-hydroxy-3-phenylpropanoic acid in analogy to the preparation of 6.
-
-
-
-
92
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85007991332
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(b) Ohyama, M.; Iinuma, K.; Suzuki, A. Biosci. Biotech. Biochem. 1994, 58, 1193-1194.
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Ohyama, M.1
Iinuma, K.2
Suzuki, A.3
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94
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0344438317
-
-
note
-
f = 0.26.
-
-
-
-
95
-
-
33847085176
-
-
Clive, D. L. J.; Chittattu, G. J.; Farina, V.; Kiel, W. A.; Menchen, S. M.; Russell, C. G.; Singh, A.; Wong, C. K.; Curtis, N. J. J. Am. Chem. Soc. 1980, 102, 4438-4447.
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Clive, D.L.J.1
Chittattu, G.J.2
Farina, V.3
Kiel, W.A.4
Menchen, S.M.5
Russell, C.G.6
Singh, A.7
Wong, C.K.8
Curtis, N.J.9
-
97
-
-
0344438314
-
-
Unpublished results
-
Addition of PhSeH to Aba residues in acyclic peptides also gives the like diastereomer selectively. For example reactions of Val-(Z)-Aba-Hpp-Hmp derivatives with PhSeH/BuLi followed by oxidation gave the corresponding (E)-isomers with ca. 5:1 diastereoselectivity (Ward, D. E.; Vázquez, A. Unpublished results).
-
-
-
Ward, D.E.1
Vázquez, A.2
-
98
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-
0000751777
-
-
Pedras, M. S. C.; Séguín-Swartz, G.; Abrams, S. R. Phytochemistry 1990, 29, 777-782.
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Phytochemistry
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Pedras, M.S.C.1
Séguín-Swartz, G.2
Abrams, S.R.3
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99
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-
0002714675
-
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Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
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J. Org. Chem.
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Still, W.C.1
Kahn, M.2
Mitra, A.3
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