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1
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59749096021
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Parts of this study have been the subjects of two preliminary communications
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Parts of this study have been the subjects of two preliminary communications:
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4
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0019991218
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13944267828
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33747888539
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Toyama, K.1
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Mase, N.3
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Takabe, K.5
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59749086999
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note
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In the preliminary experiments, (R)-4-isopropyloxazolidin-2-one (i), (S)-4-isopropyl-thiazolidin-2-thione (ii), and (1R)-2,10-camphur-sultam (iii) were examined as chiral auxiliaries in addition to (R)-4-benzyloxazolidin-2-one. However, when i was employed as a chiral source, the deconjugative asymmetric α-sulfenylation usually took place with a decreased diastereoselectivity and in a lower chemical yield than those obtained using (R)-4-benzyloxazolidin-2-one. In the case where ii was used as a chiral source, the attempted asymmetric reaction under various conditions always gave complex mixtures of the products. The asymmetric reaction employing iii as a chiral source afforded the ε-sulfenylated product corresponding to 11 (see text) as a sole product. Based on these numerous experiments, (R)-4-benzyloxazolidin-2-one was selected as the most promising chiral auxiliary. Ohata, K.; Terashima, S., unpublished results.
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23
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59749086474
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note
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4p-Me) underwent deconjugative asymmetric α-sulfenylation to give α-sulfenylated products in 84% and 53% yield, respectively, the methylsulfenyl and the (2-trimethylsilyl)ethylsulfenyl group introduced into the reaction products could not be elaborated to a thiol or an acylsulfenyl group. Ohata, K.; Terashima, S., unpublished results.{A figure is presented}
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25
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59749088474
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note
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At the design stage for this synthetic strategy, it was uncertain whether 7 or ent-7 should be selected to produce the desired 5. However, it was expected that 5 could be obtained as a major product by selecting a chiral auxiliary and by tuning the conditions for reaction.
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26
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0345304282
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Deconjugative asymmetric allylation of a dienolate with formation of a quaternary asymmetric center was recently reported by Kobayashi, et al.
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Deconjugative asymmetric allylation of a dienolate with formation of a quaternary asymmetric center was recently reported by Kobayashi, et al. Abe T., Suzuki T., Sekiguchi K., Hosokawa S., and Kobayashi S. Tetrahedron Lett. 44 (2003) 9303-9305
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(2003)
Tetrahedron Lett.
, vol.44
, pp. 9303-9305
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Abe, T.1
Suzuki, T.2
Sekiguchi, K.3
Hosokawa, S.4
Kobayashi, S.5
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84989499447
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Seebach D., Hungerbuhler E., Naef R., Schurrenberger P., Weidmann B., and Zuger M. Synthesis (1982) 138-141
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(1982)
Synthesis
, pp. 138-141
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Seebach, D.1
Hungerbuhler, E.2
Naef, R.3
Schurrenberger, P.4
Weidmann, B.5
Zuger, M.6
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33
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59749103965
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note
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In our preliminary experiments, Dieckmann condensation of the imide compound derived from 5 by sequential deacetalization, retro-Michael reaction, and acylation without transesterification were attempted to produce 1. However, since the leaving ability of the imide moiety toward nucleophilic attack of the α-carbanion of thioester was insufficient for Dieckmann condensation under various conditions, we decided to subject the corresponding ester 3, which had a leaving ability superior to that of the imide compound, to Dieckmann condensation.
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34
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59749097466
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note
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In addition to benzyl ester 15, some other esters (methyl, ethyl, and isopropyl ester) were synthesized in a similar manner. Since the thiols derived from these esters by sequential deacetalization and retro-Michael reaction were fairly volatile and unstable, the chemical yield of the acylated compound carrying a methyl, ethyl or isopropyl ester was found to be lower than that for 3 bearing a benzyl ester.
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35
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59749091116
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note
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1H NMR spectrum (see Experimental).
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36
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59749102046
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note
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3 as an alkali metal base. However, all these bases were found to be not effective for this retro-Michael reaction.
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37
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0019979856
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Sasaki H., Oishi H., Hayashi T., Matsuura I., Ando K., and Sawada M. J. Antibiot. 35 (1982) 396-400
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(1982)
J. Antibiot.
, vol.35
, pp. 396-400
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Sasaki, H.1
Oishi, H.2
Hayashi, T.3
Matsuura, I.4
Ando, K.5
Sawada, M.6
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38
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59749093038
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note
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Determination of MICs by agar dilution methods was performed according to the guideline M7-A6 of the Clinical and Laboratory Standards Institute (2003).
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39
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0031793850
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14C] acetate into cellular fatty acid as previously described with some modifications. See
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14C] acetate into cellular fatty acid as previously described with some modifications. See,. Murakami K., Tobe K., Ide T., Mochizuki T., Ohashi M., Akanuma Y., Yazaki Y., and Kadowaki T. Diabates 47 (1998) 1841-1847
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(1998)
Diabates
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, pp. 1841-1847
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Murakami, K.1
Tobe, K.2
Ide, T.3
Mochizuki, T.4
Ohashi, M.5
Akanuma, Y.6
Yazaki, Y.7
Kadowaki, T.8
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41
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0034724397
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Kuhajda F.P., Pizer E.S., Li J.N., Mani S., Frehywot G.L., and Townsend C.A. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 3450-3454
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Kuhajda, F.P.1
Pizer, E.S.2
Li, J.N.3
Mani, S.4
Frehywot, G.L.5
Townsend, C.A.6
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42
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0035935202
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Sakya S.M., Suarez-Contreras M., Dirlam J.P., O'Connell T.N., Hayashi S.F., Santoro S.L., Kamicker B.J., George D.M., and Ziegler C.B. Bioorg. Med. Chem. Lett. 11 (2001) 2751-2754
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Sakya, S.M.1
Suarez-Contreras, M.2
Dirlam, J.P.3
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Hayashi, S.F.5
Santoro, S.L.6
Kamicker, B.J.7
George, D.M.8
Ziegler, C.B.9
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43
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30444441272
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Kim P., Zhang Y.-M., Shenoy G., Nguyen Q.-A., Boshoff H.I., Manjunatha U.H., Goodwin M.B., Lonsdale J., Price A.C., Miller D.J., Duncan K., White S.W., Rock C.O., Barry III C.E., and Dowd C.S. J. Med. Chem. 49 (2006) 159-171
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Kim, P.1
Zhang, Y.-M.2
Shenoy, G.3
Nguyen, Q.-A.4
Boshoff, H.I.5
Manjunatha, U.H.6
Goodwin, M.B.7
Lonsdale, J.8
Price, A.C.9
Miller, D.J.10
Duncan, K.11
White, S.W.12
Rock, C.O.13
Barry III, C.E.14
Dowd, C.S.15
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