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Paquette, L.A.1
Gao, Z.2
Ni, Z.3
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2
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2642617084
-
-
Spinosyn A is presently being marketed by DowElanco Inc.
-
Spinosyn A is presently being marketed by DowElanco Inc.
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-
-
-
3
-
-
2642701818
-
-
7) have been recently abandoned in favor of spinosyn A (Kirst, H. A.; communication dated June 7, 1994)
-
7) have been recently abandoned in favor of spinosyn A (Kirst, H. A.; communication dated June 7, 1994).
-
-
-
-
4
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-
2642613769
-
-
The LY232105 label was assigned following initial discovery of this secondary metabolite in the Eli Lilly laboratories
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The LY232105 label was assigned following initial discovery of this secondary metabolite in the Eli Lilly laboratories.
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5
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0025917476
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Kirst, H. A.; Michel, K. H.; Martin, J. W.; Creemer, L. C.; Chio, E. H.; Yao, R. C.; Nakatsukasa, W. M.; Boeck, L. D.; Occolowitz, J. L.; Paschal, J. W.; Deeter, J. B.; Jones, N. D.; Thompson, G. D. Tetrahedron Lett. 1991, 32, 4839.
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Nakatsukasa, W.M.7
Boeck, L.D.8
Occolowitz, J.L.9
Paschal, J.W.10
Deeter, J.B.11
Jones, N.D.12
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Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1992, 114, 2260; 1993, 115, 4497.
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Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1992, 114, 2260; 1993, 115, 4497.
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8
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2642675357
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The authors thank Dr. Graham F. Smith for these studies
-
The authors thank Dr. Graham F. Smith for these studies.
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13
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33947092680
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Organic Syntheses
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21
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2642640548
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Unpublished work from this laboratory
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Purdie, M. Unpublished work from this laboratory.
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Purdie, M.1
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22
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2642607131
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Unpublished work from this laboratory
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Collado, I. Unpublished work from this laboratory.
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Collado, I.1
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23
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2642647183
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NOE experiments designed to reveal the stereochemistry of this αβ-epoxy ketone proved not to be definitive
-
NOE experiments designed to reveal the stereochemistry of this αβ-epoxy ketone proved not to be definitive.
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-
-
-
24
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2642642229
-
-
note
-
In an effort to bypass lactol formation as in 20, the primary hydroxyl group in 19 was protected as the PMB derivative. This intermediate was not utilized further when it was recognized that oxidative cleavage of its 1,2-diol moiety with sodium periodate provided the aldehyde in only 22% yield for the two steps.
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-
-
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25
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2642638880
-
-
Remarkably, when lithium hexamethyldisilazide was employed as the base, only the corresponding ring-closed silyl acetal was produced (92%) as a mixture of two isomers
-
Remarkably, when lithium hexamethyldisilazide was employed as the base, only the corresponding ring-closed silyl acetal was produced (92%) as a mixture of two isomers.
-
-
-
-
26
-
-
2642679375
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-
note
-
Other methods for the enolate oxidation of 20 were briefly examined. Examples include deprotonation with potassium hexamethyldisilazide and subsequent exposure of the enolate anion to oxygen or the Davis oxaziridine. However, subsequent sodium periodate oxidation in these cases proceeded in only 34% and 15% yield, respectively.
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28
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2642618711
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note
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16 (equation presented)
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35
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33847089947
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36
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33847089947
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3: (a) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179. (b) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561.
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Hiyama, T.1
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0002899916
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Wulff, W. D.; Peterson, G. A.; Bauta, W. E.; Chan, K.-S.; Faron, K. L.; Gilbertson, S. R.; Kaesler, R. W.; Yang, D. C.; Murray, C. K. J. Org. Chem. 1986, 51, 277.
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Yang, D.C.8
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0025134909
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For selected examples, see: (a) ref 7. (b) Masamune, S.; Yamamoto, H.; Kamata, S.; Fukuzawa, A. J. Am. Chem. Soc. 1975, 97, 3513. (c) Woodward, R. B. et al. J. Am. Chem. Soc. 1981, 103, 3215.
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