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0141694744
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note
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To achieve an efficient alkylation with iodide 18, incorporation of an electron-donating 4-methoxy group into the aryl acetate was required. The subsequent aldol coupling of 5 with 6 and ester reduction steps proceeded in comparable yield to that obtained previously for the corresponding Heathcock aryl ester (ref 6a).
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34
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0141583083
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note
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To date, we have performed this key aldol coupling on a gram scale. In contrast, by using the lithium enolate from 3, the addition proceeds under Felkin-Anh induction from the aldehyde 2 and leads to exclusively the undesired (SR) configuration.
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