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Biologically active 1-subsutituted tetrahydroisoquinoline alkaloids, (-)-trolline, (-)-crispine A, and (-)-crispine E were synthesized using a chiral isoquinolinecarbaldehyde as a key material.The aldehyde was readily obtained from a 1-cyanoisoquinoline, and subjected to a Horner-Wadsworth-Emmons reaction.The chiral tetrahydroisoquinoline derivative thus obtained was used for the synthesis of the optically active isoquinoline alkaloids.
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Itoh et al. (2007) studied this question.
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