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25
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85088172604
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note
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2 afforded the corresponding alcohol in only 32% yield. The major side product was the desilylation product.
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26
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0024448725
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85088175485
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note
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2-NEt, DMAP, and tBuOH; and (3) removal of Cbz group by hydrogenation over 10% Pd-C in MeOH (55% overall).
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31
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0442283630
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Reaction rate was accelerated in the presence of a trace amount of water
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Reaction rate was accelerated in the presence of a trace amount of water.
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32
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85088175335
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note
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2O in EtOAc followed by saponification with aqueous LiOH at 23°C for 30 min (90% overall).
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33
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85088175626
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note
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2O (6:1) for 30 min followed by reaction with BnBr in DMF at 0 °C (91%).
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35
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0442315110
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note
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The major epoxide was cleanly separated by an isocratic reverse phase HPLC (see ref 8g for similar separation) on a YMC-Pack ODS-AQ 5S 120 Å column (4.6 × 250 mm) with flow rate 1 mL/min and UV detection at 254 nm. Retention times for 2: 31.58 min; and diastereomer: 37.20 min.
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