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1
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Son, B.W.1
Jensen, P.R.2
Kauffman, C.A.3
Fenical, W.4
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6
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64849110380
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For other representative syntheses of epidithiodiketo-piperazines, see (35) and references cited therein
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For other representative syntheses of epidithiodiketo-piperazines, see (35) and references cited therein.
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-
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7
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64849103733
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For a recent total synthesis of a sulfur containing diketopiperazine, see 36
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For a recent total synthesis of a sulfur containing diketopiperazine, see (36).
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9
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0014834471
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K. Katagiri, K. Sato, S. Hayakawa, T. Matsushima, H. Minato, J. Antibiot. (Tokyo) 23, 420 (1970).
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Katagiri, K.1
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Matsushima, T.4
Minato, H.5
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10
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4444344599
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P. S. Steyn, Ed, Academic Press, New York
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G. W. Kirby, D. J. Robins, in The Biosynthesis of Mycotoxins: A Study in Secondary Metabolism, P. S. Steyn, Ed. (Academic Press, New York, 1980), p. 301.
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The Biosynthesis of Mycotoxins: A Study in Secondary Metabolism
, pp. 301
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Kirby, G.W.1
Robins, D.J.2
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11
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0000663548
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J. D. Herscheid, R. J. Nivard, M. W. Tijhuis, H. P. Scholten, H. C. Ottenheijm, J. Org. Chem. 45, 1880 (1980).
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Herscheid, J.D.1
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Tijhuis, M.W.3
Scholten, H.P.4
Ottenheijm, H.C.5
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14
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33845551868
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D. Seebach, M. Boes, R. Naef, W. B. Schweizer, J. Am. Chem. Soc. 105, 5390 (1983).
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Seebach, D.1
Boes, M.2
Naef, R.3
Schweizer, W.B.4
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15
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64849093641
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Sensitivity of diketopiperazine to epimerization at the tryptophan-derived Ca-methine is highlighted by isolation of the corresponding diastereomer of 12 in 11% yield
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Sensitivity of diketopiperazine to epimerization at the tryptophan-derived Ca-methine is highlighted by isolation of the corresponding diastereomer of 12 in 11% yield.
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-
-
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16
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64849096789
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The major isolable side product is the C3-reduction product. Although the use of tetrahydrofuran (THF) as solvent provided a higher yield of dimer (+)-13 (52%) on <1 g scale, the yields of larger scale reactions (>1 g scale) in THF were lower (40%).
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The major isolable side product is the C3-reduction product. Although the use of tetrahydrofuran (THF) as solvent provided a higher yield of dimer (+)-13 (52%) on <1 g scale, the yields of larger scale reactions (>1 g scale) in THF were lower (40%).
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17
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0033551437
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A. Rauk et al., Biochemistry 38, 9089 (1999).
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Rauk, A.1
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22
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64849104478
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All attempts at the conversion of tetraene 26 to 1 based on the chemistry developed (fig. S5) in the synthesis of 23 failed, highlighting the additional challenges of the dimeric series.
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All attempts at the conversion of tetraene 26 to 1 based on the chemistry developed (fig. S5) in the synthesis of 23 failed, highlighting the additional challenges of the dimeric series.
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26
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64849086467
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In addition to the desired, 11S,11'S,15S, 15'S)-18, the corresponding (11R,11'S,15R,15'S)-18a and (11R,11'R,15R,15'R)-18b diastereomers were also isolated 18:18a:18b, 25:7:1, Exposure of any diastereomer to the reaction conditions does not result in equilibration
-
In addition to the desired (+)-(11S,11'S,15S, 15'S)-18, the corresponding (11R,11'S,15R,15'S)-18a and (11R,11'R,15R,15'R)-18b diastereomers were also isolated (18:18a:18b, 25:7:1). Exposure of any diastereomer to the reaction conditions does not result in equilibration.
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27
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64849104654
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The expected 1,3-oxazolidine-2-thione (20) was observed in the product mixture.
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The expected 1,3-oxazolidine-2-thione (20) was observed in the product mixture.
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30
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0036008124
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H. Chen, B. K. Hubbard, S. E. O'Connor, C. T. Walsh, Chem. Biol. 9, 103 (2002).
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Chen, H.1
Hubbard, B.K.2
O'Connor, S.E.3
Walsh, C.T.4
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31
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0035852639
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A. Schoendorf, C. D. Rithner, R. M. Williams, R. B. Croteau, Proc. Natl. Acad. Sci. U.S.A. 98, 1501 (2001).
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Schoendorf, A.1
Rithner, C.D.2
Williams, R.M.3
Croteau, R.B.4
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34
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21244435263
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Y. Chen, Z. Miao, W. Zhao, J. Ding, FEBS Lett. 579, 3683 (2005).
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Chen, Y.1
Miao, Z.2
Zhao, W.3
Ding, J.4
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37
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64849083100
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M.M. is an Alfred P. Sloan Research Fellow and a Beckman Young Investigator. J.K. and J.A.A. acknowledge predoctoral (National Defense Science and Engineering Graduate) and postdoctoral [Fonds québécois de la recherche sur la nature et les technologies (FQRNT, fellowships, respectively. We thank P. Müller for assistance with x-ray structures of, )-1 and, )-14. We acknowledge generous support from Amgen, AstraZeneca, Boehringer Ingelheim, GlaxoSmithKline, Merck, and Lilly. Structural parameters for and, )-14 are freely available from the Cambridge Crystallographic Data Centre under CCDC-719219 and CCDC-719218, respectively
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M.M. is an Alfred P. Sloan Research Fellow and a Beckman Young Investigator. J.K. and J.A.A. acknowledge predoctoral (National Defense Science and Engineering Graduate) and postdoctoral [Fonds québécois de la recherche sur la nature et les technologies (FQRNT)] fellowships, respectively. We thank P. Müller for assistance with x-ray structures of (+)-1 and (+)-14. We acknowledge generous support from Amgen, AstraZeneca, Boehringer Ingelheim, GlaxoSmithKline, Merck, and Lilly. Structural parameters for and (+)-14 are freely available from the Cambridge Crystallographic Data Centre under CCDC-719219 and CCDC-719218, respectively.
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