Abstract
The concise total synthesis of (+/-)-crinine was accomplished in 24% overall yield and eleven steps starting from an easily available allylic alcohol. The key step of the current synthesis involved the NBS-promoted semipinacol rearrangement reaction of allylic alcohols. The hydroindole skeleton with the sterically congested quaternary carbon center was established concisely by utilizing this semipinacol rearrangement followed by a combination of intramolecular aldol and aza-Michael reactions.
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