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33644906057
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note
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β-Hydride elimination is probably the reason, though we did not obtain any evidence for the production of 3-cyclopentenon.
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40
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33644914925
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-
note
-
13C NMR spectroscopy (δ 126.3 and 133.4), which is probably responsible for the trans olefin isomer.
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41
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18844410382
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33644927155
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51
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33644913580
-
-
note
-
3 in the transition state (B ) assisted the syn elimination effectively.
-
-
-
-
52
-
-
33644910346
-
-
note
-
Deprotection of the TBS group with TBAF in THF and with NBS in wet DMSO was unsuccessful.
-
-
-
-
53
-
-
33644904245
-
-
note
-
The stereochemistry of the newly formed olefin at C(13) was assigned by the chemical shift of the C(13)-H: (E)-isomer 31, δ 6.87 (d, J=11 Hz); (Z)-isomer 34, δ 6.43 (d, J=11 Hz).
-
-
-
-
54
-
-
84985521848
-
-
The corresponding alcohol is synthesized in racemic form with low product selectivity in low yield: H. Mayr, and B. Grubmüller Angew. Chem., Int. Ed. Engl. 17 1978 130 131
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Mayr, H.1
Grubmüller, B.2
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