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19844374227
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The approach described in reference [9] also takes advantage of an all-encompassing IMDA
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The approach described in reference [9] also takes advantage of an all-encompassing IMDA.
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19844379820
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note
-
We thank DSM Fine Chemicals (Geleen) for a generous gift of the enantiomerically pure material (98% ee according to Mosher's ester).
-
-
-
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29
-
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19844368406
-
-
note
-
The enantiomeric purity of (-)-13 was confirmed via chiral HPLC analysis (2,6-TBS-3-methyl-γ-cyclodextrin 50%/50% OV-1710).
-
-
-
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31
-
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85082860156
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Substance 11 is rather unstable; while it can be usually stored on copper in the dark at 0 °C for a couple of weeks, some batches were found to decompose upon distillation. A more tedious but reliable procedure involves the use of Schwartz reagent (74% yield): E. Nigishi, T. Takahashi, Synthesis 1988, 1-19.
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Nigishi, E.1
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1542504084
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The use of dimethyl-1-diazo-2-oxopropylphosphonate (ref. [25a]), prepared according to reference [25b], led to a high yield of a 4:1 mixture in favour of the cis derivative. -[25a] S. Müller, B. Liepold, G. J. Roth, H. J. Bestmann, Synlett. 1996, 521-522. -
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37
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19844368781
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note
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1H NMR analysis using (S)-mandelic acid methyl ether as shift reagent.
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38
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39
-
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19844362260
-
-
note
-
A similar Stille coupling (46% yield) involving (+)-2 has been described before in the context of the preparation of (+)-hamabiwalactone B (ref. [17]).
-
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-
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40
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33847801898
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19844363915
-
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note
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For the sake of consistency the numbering of the acyclic precursor 5 is maintained in the cycloadducts 17 and in the subsequent intermediates.
-
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43
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84986437005
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44
-
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19844372791
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note
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The α-orientation of the methoxy group has been assigned in the c-series, see footnote 39 in reference [8b]; see also reference [6c].
-
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45
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0001209154
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46
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19844362490
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note
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Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-153103. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: int.code+44(1223)336-033; E-mail: deposit@ccdc.cam.ac.uk].
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