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A strategy for synthesizing the tricyclic fragment 5 of atropurpuran 1 is reported. Rings A and C of atropurpuran were assembled stereoselectively via two intramolecular Michael additions. The advanced tricyclic skeleton 5 shows the correct functionality and stereochemistry for atropurpuran 1, so the skeleton may serve as a key intermediate in its total synthesis.
A practical asymmetric synthesis of the trans-fused 2-methyl-5-hydroxyldecahydroquinolines 8a and 8b is reported. Double Michael addition of enone 4 with (S)-phenylethylamine generated separable C2-methylated decahydroquinolinones 5a and 5b, which were converted to 8a and 8b via several functional group transformations.
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