A pivotal intramolecular Michael addition to form a fused 5,7,5 ring system and the skeleton of (−)-galanthamine (1) was completely controlled by a remote chiral imidazolidinone auxiliary derived from D-phenylalanine (see scheme). This total synthesis of the allylic alcohol 1 avoids the corresponding enone narwedine, a highly allergenic intermediate in previous syntheses of 1.
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Kodama et al. (2004) studied this question.
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