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Goetz, G. H.; Harrigan, G. G.; Likos, J. J.; Kasten, T. P. PCT WO 03/051831; Chem. Abstr. 2003, 139, 47155.
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2
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1642619511
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For other natural chloroleucines and their occurrence in Dysidea sponges, see: and references cited therein
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For other natural chloroleucines and their occurrence in Dysidea sponges, see:. Ardá A., Jiménez C., and Rodríguez J. Tetrahedron Lett. 45 (2004) 3241-3243 and references cited therein
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Ardá, A.1
Jiménez, C.2
Rodríguez, J.3
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5
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0037073204
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Carroll A.R., Pierens G.K., Fechner G., Leone P.A., Ngo A., Simpson M., Hyde E., Hooper J.N.A., Boström S.-L., Musil D., and Quinn R.J. J. Am. Chem. Soc. 124 (2002) 13340-13341
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Carroll, A.R.1
Pierens, G.K.2
Fechner, G.3
Leone, P.A.4
Ngo, A.5
Simpson, M.6
Hyde, E.7
Hooper, J.N.A.8
Boström, S.-L.9
Musil, D.10
Quinn, R.J.11
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6
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0037073167
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Hanessian S., Margarita R., Hall A., Johnstone S., Tremblay M., and Parlanti L. J. Am. Chem. Soc. 124 (2002) 13342-13343
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Hanessian, S.1
Margarita, R.2
Hall, A.3
Johnstone, S.4
Tremblay, M.5
Parlanti, L.6
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9
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0037810287
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We have argued that the structures for aeruginosins 205 should be revised, since when the claimed 6-chlorooctahydroindole ring in the proposed structures was synthesized, its NMR data did not agree with those reported for the azabicyclic amino acid of the aforementioned natural products. For the synthesis of the putative core of aeruginosins 205, see:
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We have argued that the structures for aeruginosins 205 should be revised, since when the claimed 6-chlorooctahydroindole ring in the proposed structures was synthesized, its NMR data did not agree with those reported for the azabicyclic amino acid of the aforementioned natural products. For the synthesis of the putative core of aeruginosins 205, see:. Valls N., Vallribera M., Font-Bardía M., Solans X., and Bonjoch J. Tetrahedron: Asymmetry 14 (2003) 1241-1244
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Valls, N.1
Vallribera, M.2
Font-Bardía, M.3
Solans, X.4
Bonjoch, J.5
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11
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0000512182
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For the synthesis of 3-substituted threonines from threonines via aziridine intermediates, see:
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For the synthesis of 3-substituted threonines from threonines via aziridine intermediates, see:. Wakamiya T., Shimbo K., Shiba T., Nakajima K., Neya M., and Okawa K. Bull. Chem. Soc. Jpn 55 (1982) 3878-3881
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Wakamiya, T.1
Shimbo, K.2
Shiba, T.3
Nakajima, K.4
Neya, M.5
Okawa, K.6
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13
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0001593856
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For the reactivity of β-lactones derived from l-threonine and related amino acids, see:
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For the reactivity of β-lactones derived from l-threonine and related amino acids, see:. Pansare S.V., and Vederas J.C. J. Org. Chem. 54 (1989) 2311-2316
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Pansare, S.V.1
Vederas, J.C.2
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Higashibayashi S., Kohno M., Goto T., Suzuki K., Mori T., Hashimoto K., and Nakata M. Tetrahedron Lett. 45 (2004) 3707-3712
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Higashibayashi, S.1
Kohno, M.2
Goto, T.3
Suzuki, K.4
Mori, T.5
Hashimoto, K.6
Nakata, M.7
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16
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33646113337
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note
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15
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0032474861
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Shreder K., Zhang L., Dang T., Yaksh T.L., Umeno H., DeHaven R., Daubert J., and Goodman M. J. Med. Chem. 41 (1998) 2631-2635
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Shreder, K.1
Zhang, L.2
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Umeno, H.5
DeHaven, R.6
Daubert, J.7
Goodman, M.8
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0001496779
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Shao H., Wang S.H.H., Lee C.-W., Ösapay G., and Goodman M. J. Org. Chem. 60 (1995) 2956-2957
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Shao, H.1
Wang, S.H.H.2
Lee, C.-W.3
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Goodman, M.5
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24
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0036376938
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Chaltin P., Lescrinier E., Lescrinier T., Rozenski J., Hendrix C., Rosemeyer H., Busson R., Van Aerschot A., and Herdewijn P. Helv. Chim. Acta 85 (2002) 2258-2283
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Helv. Chim. Acta
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Chaltin, P.1
Lescrinier, E.2
Lescrinier, T.3
Rozenski, J.4
Hendrix, C.5
Rosemeyer, H.6
Busson, R.7
Van Aerschot, A.8
Herdewijn, P.9
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30344479954
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Schneider A., Rodrigues O.E.D., Paixao M.W., Appelt H.R., Braga A.L., and Wessjohann L.A. Tetrahedron Lett. 47 (2006) 1019-1021
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Schneider, A.1
Rodrigues, O.E.D.2
Paixao, M.W.3
Appelt, H.R.4
Braga, A.L.5
Wessjohann, L.A.6
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26
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0033591141
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For a review on the synthesis of optically active β-lactones, see:
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For a review on the synthesis of optically active β-lactones, see:. Yang H.W., and Romo D. Tetrahedron 55 (1999) 6403-6434
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(1999)
Tetrahedron
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Yang, H.W.1
Romo, D.2
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0025971901
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For the synthesis of β-substituted N-protected α-amino-β-lactones promoted by treatment of N-(o-nitrophenyl)sulfenyl derivatives of β-hydroxy α-amino acids with 4-bromobenzenesulfonyl chloride, see:
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For the synthesis of β-substituted N-protected α-amino-β-lactones promoted by treatment of N-(o-nitrophenyl)sulfenyl derivatives of β-hydroxy α-amino acids with 4-bromobenzenesulfonyl chloride, see:. Pu Y., Martin F.M., and Vederas J.C. J. Org. Chem. 56 (1991) 1280-1283
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J. Org. Chem.
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Pu, Y.1
Martin, F.M.2
Vederas, J.C.3
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33646096695
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note
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34
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23044499419
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Reddy L.R., Saravanan P., Fournier J.-F., Reddy B.V.S., and Corey E.J. Org. Lett. 7 (2005) 2703-2705
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Org. Lett.
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Reddy, L.R.1
Saravanan, P.2
Fournier, J.-F.3
Reddy, B.V.S.4
Corey, E.J.5
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33646099110
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note
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2O, see Ref. 9a.
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39
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33646099786
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note
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2), 84.6 (C4), 128.5, 128.7, 128.8, 135.8 (Ar), 155.6 (CO), 168.8 (C2). All new compounds were characterized by HRMS or microanalysis.
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40
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33646116501
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note
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2), 128.0, 128.3, 128.5, 135.7 (Ar), 156.8 (NCO), 173.6 (C1).
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41
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0030722006
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For the synthesis of (2R,3S)- and (2S,3R)-2-amino-3-chlorobutanoic acid (β-chlorothreonines) by optical resolution of the racemic form, see:
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For the synthesis of (2R,3S)- and (2S,3R)-2-amino-3-chlorobutanoic acid (β-chlorothreonines) by optical resolution of the racemic form, see:. Shiraiwa T., Miyazaki H., Ohta A., Motonaka K., Kobayashi E., Kubo M., and Kurokawa H. Chirality 9 (1997) 656-660
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(1997)
Chirality
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Shiraiwa, T.1
Miyazaki, H.2
Ohta, A.3
Motonaka, K.4
Kobayashi, E.5
Kubo, M.6
Kurokawa, H.7
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42
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84981836174
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5:
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5:. Plattner Pl.A., Boller A., Frick H., Fürst A., Hegedüs B., Kirchensteiner H., Majnoni St., Schläpfer R., and Spiegelberg H. Helv. Chim. Acta 40 (1957) 1531-1552
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(1957)
Helv. Chim. Acta
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Plattner, Pl.A.1
Boller, A.2
Frick, H.3
Fürst, A.4
Hegedüs, B.5
Kirchensteiner, H.6
Majnoni, St.7
Schläpfer, R.8
Spiegelberg, H.9
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44
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0037196315
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To our knowledge there is only one precedent of β-lactonization of 3-hydroxyleucine derivatives in the literature, involving the (2S,3S)-N,N-dibenzyl derivative:
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To our knowledge there is only one precedent of β-lactonization of 3-hydroxyleucine derivatives in the literature, involving the (2S,3S)-N,N-dibenzyl derivative:. Laib T., Chastanet J., and Zhu J. J. Am. Chem. Soc. 124 (2002) 583-590
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(2002)
J. Am. Chem. Soc.
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Laib, T.1
Chastanet, J.2
Zhu, J.3
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33646117453
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note
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2O); NMR data, see Table 1.
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46
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0035898158
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For the enantioselective synthesis of the four stereoisomeric 3-hydroxyleucines, see:
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For the enantioselective synthesis of the four stereoisomeric 3-hydroxyleucines, see:. Makino K., Okamoto N., Hara O., and Hamada Y. Tetrahedron: Asymmetry 12 (2001) 1757-1762
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(2001)
Tetrahedron: Asymmetry
, vol.12
, pp. 1757-1762
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Makino, K.1
Okamoto, N.2
Hara, O.3
Hamada, Y.4
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47
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33646100953
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note
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2), 128.4, 128.7, 128.9, 136.2 (Ar), 156.9 (NCO), 175.2 (C-1). Compound 2, see Table 1. LC-MS of the product indicated that a small amount of an N-ethyl derivative had formed.
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48
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0032885574
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For the synthesis of (2S,3S)-(+)-3-fluoroleucine, see:
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For the synthesis of (2S,3S)-(+)-3-fluoroleucine, see:. Davis F.A., Srirajan V., and Titus D.D. J. Org. Chem. 64 (1999) 6931-6934
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(1999)
J. Org. Chem.
, vol.64
, pp. 6931-6934
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Davis, F.A.1
Srirajan, V.2
Titus, D.D.3
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