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2942562806
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17and 18wasdeterminedbyHPLCanalysisusingchiralcolumns(CHIRALCELAD[DAICEL] for 18,CHIRALCELOD-H[DAICEL]forbenzoateesterof 17)
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Enantiomeric purity of 17 and 18 was determined by HPLC analysis using chiral columns (CHIRALCEL AD [DAICEL] for 18, CHIRALCEL OD-H [DAICEL] for benzoate ester of 17)
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37
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2942529411
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note
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Slight lowering of the enantiomeric purity was observed in the Mitsunobu reaction step
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38
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2942622647
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Since epoxide 18 was used as it stood (88-92% ee), the optical purity of 4 was same as that of 18. Although the minor enantiomer of 4 produced small amounts of undesired diastereomers, which were inseparable from 25, in the connection reaction with 5, these were facilely separated from 26 at the C-ring cyclization step
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Since epoxide 18 was used as it stood (88-92% ee), the optical purity of 4 was same as that of 18. Although the minor enantiomer of 4 produced small amounts of undesired diastereomers, which were inseparable from 25, in the connection reaction with 5, these were facilely separated from 26 at the C-ring cyclization step
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43
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2942568395
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26toproduceasignificantamountofthecorrespondingC18-exomethylenederivative
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Prolonged reaction time resulted in elimination of the TBSO group at C18 of 26 to produce a significant amount of the corresponding C18-exomethylene derivative
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46
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2942531116
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2, heating,orchangingconcentrationof 28andreagents)showednoeffect
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2, heating, or changing concentration of 28 and reagents) showed no effect
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