Enantioselective total syntheses and X-ray structures of both (S)-tetrahydropalmatrubine (2) and (S)-corytenchine (3) are reported for the first time. They were both derived from (S)-N-norlaudanidine, a benzyltetrahydroisoquinoline that was synthesized with high (>95% ee) enantioselectivity using a chiral auxiliary-assisted Bischler-Napieralski cyclization/reduction approach.
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September 2010
The title compound, C(13)H(18)BNO(4), was readily obtained from the reaction of methyl 4-boronobenzene acetate with ethano-lamine. A combination of inter-molecular N-H⋯O hydrogen bonds and C-H⋯π inter-actions leads to the pairwise association of mol-ecules.
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