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(a) Sun, D.; Hansen, M.; Clement, J.; Hurley, L. H. Biochemistry 1993, 32, 8068.
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(a) Furukawa, M.; Hayakawa, I.; Ohta, G.; Iitaka, Y. Tetrahedron 1975, 31, 2989.
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Furukawa, M.1
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Iitaka, Y.4
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14
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24044536953
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For another synthesis of the altromycin branched C-glycoside substructure, see the following communication: Koo, B.; McDonald, F. E. Org. Lett. 2005, 7, 3621.
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Koo, B.1
McDonald, F.E.2
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17
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0023777727
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(a) Gilbreath, S. G.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1988, 110, 6172.
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Gilbreath, S.G.1
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18
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0023683866
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(b) Harris, T. M.; Harris, C. M.; Kuzma, P. C.; Lee, J. Y. C.; Mahalingam, S.; Gilbreath, S. G. J. Am. Chem. Soc. 1988, 110, 6186.
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Harris, T.M.1
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Kuzma, P.C.3
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Mahalingam, S.5
Gilbreath, S.G.6
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19
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0001141796
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(c) Yamaguchi, M.; Hasebe, K.; Higashi, H.; Uchida, M.; Irie, A.; Minami, T. J. Org. Chem. 1990, 55, 1611.
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Yamaguchi, M.1
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Higashi, H.3
Uchida, M.4
Irie, A.5
Minami, T.6
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21
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0023831584
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For similar examples of this addition - elimination reaction, see: (a) Hormi, O. E. O. J. Org. Chem. 1988, 53, 880.
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Hormi, O.E.O.1
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23
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0347545735
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For mechanistic discussion, see: Rappoport, Z. Acc. Chem. Res. 1992, 25, 474.
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Rappoport, Z.1
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26
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24044544320
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Devos, A.; Frisque-Hesbain, A.-M.; Colens, A.; Ghosez, L. J. Chem. Soc., Chem. Commun. 1979, 1180.
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Devos, A.1
Frisque-Hesbain, A.-M.2
Colens, A.3
Ghosez, L.4
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27
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33645604999
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note
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Attempted isomerization of 16 to the conjugated isomer 15 was unsuccessful under acidic or basic conditions.
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28
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4444276636
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Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
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Kolb, H.C.1
VanNieuwenhze, M.S.2
Sharpless, K.B.3
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30
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33645589905
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note
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As the absolute stereochemistry of the C14-C16 epoxide of altromycin has not been established, it is desirable to synthesize both epoxide enantiomers of 1. Thus, treatment of 19 with AD-mix-α under the same conditions produced ent-20 (12:1 er), which was converted into ent-1.
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31
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33847085007
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(a) Node, M.; Nishide, K.; Fuji, K.; Fujita, E. J. Org. Chem. 1980, 45, 4275.
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J. Org. Chem.
, vol.45
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Node, M.1
Nishide, K.2
Fuji, K.3
Fujita, E.4
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32
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33645597814
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note
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(b) The use of ethanethiol (ref 17a) resulted in ethanethiol substitution at Cl2 as the sole product, but the more bulky tert-butanethiol was successfully applied to give only 21.
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-
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33
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33645595574
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note
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Tris-TIPS-protected intermediate was unstable and air oxidized to tris-TIPS-protected quinone during attempted product isolation.
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-
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36
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33645583484
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see Supporting Information
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Structure assignment was determined by NOE analysis of compound 25 (see Supporting Information).
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38
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33645601946
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note
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Use of methylmagnesium bromide occasionally resulted in significant amounts of a byproduct from conjugate addition of methyl Grignard to the C16-C14 alkene under extended reaction times.
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