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18
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0028316585
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3SnCl 78% (Cabezas, J. A.; Oehlschlager, A. C. Synthesis 1994, 432); ethynyl(tributyl)tin, n-BuSnH, AIBN 96% (Corey, E. J.; Wollenberg, R. H. J. Am. Chem. Soc. 1974, 96, 5581).
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Cabezas, J.A.1
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19
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33847805703
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3SnCl 78% (Cabezas, J. A.; Oehlschlager, A. C. Synthesis 1994, 432); ethynyl(tributyl)tin, n-BuSnH, AIBN 96% (Corey, E. J.; Wollenberg, R. H. J. Am. Chem. Soc. 1974, 96, 5581).
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20
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0342907668
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note
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3, MeOH.
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23
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0040746033
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25
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8044249421
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26
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0001616071
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Yamaguchi, M.5
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27
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0343342765
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note
-
2 purchased from Merck Schuchardt or Aldrich (>99.9%) and dried at 1 mmHg and 250°C for 4 h immediately prior to use.
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-
-
-
28
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0342473313
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note
-
1H NMR data of aspinolide B which displays H8 at 4.94 ppm as a double dublet (J = 9.0, 8.0 Hz), characteristic of trans diaxial orientation. In comparison, H8 in 24a (δ 3.83 ppm) appears as double triplet (J = 8.5, 8.5, 5.0 Hz) while in 24b (δ 4.30 ppm) as a singlet.
-
-
-
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29
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0342907667
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note
-
Mitsunobu reaction carried out with crotonic acid instead of p-NBA was unsucessfull.
-
-
-
-
30
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0342473314
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note
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D -19.1 (c 1.0, MeOH)).
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31
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0001599010
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Stammen, B.; Berlage, U.; Kindermann, R.; Kaiser, M.; Günther, M.; Sheldrick, W. S.; Welzel, P.; Roth, W. R. J. Org. Chem. 1992, 57, 6566.
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Stammen, B.1
Berlage, U.2
Kindermann, R.3
Kaiser, M.4
Günther, M.5
Sheldrick, W.S.6
Welzel, P.7
Roth, W.R.8
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