Abstract l-Serine was transformed in 8 steps into (4R,5S)-2,2-dimethyl-4-[(Z)-3-pentadecenyl]-1,3-dioxan-5-amine. This chiral ε,ζ-unsaturated amine was subjected to intramolecular aminomercuration and then acid hydrolysis to give (−)-deoxoprosopinine and (−)-deoxoprosophylline.
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Saitoh et al. (1981) studied this question.
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