Awesome Chemistry Experiments For 6,7-Dimethoxy-3,4-dihydroisoquinoline

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Synthesis of both enantiomers of protoberberines via laterally lithiated (S)-4-isopropyl-2-(o-tolyl)-oxazolines

The addition of the laterally lithiated (S)-4-isopropyl-2-(o- tolyl)oxazoline (1) to 6,7-dimethoxy-3,4-dihydroisoquinoline (2) proceeded in modest diastereoselectivity. However, the addition products (3a) and (3b) were easily separated by column chromatography over silica gel. Acid-catalyzed lactamization of 3a and 3b followed by LiAlH4-reduction afforded the corresponding optically pure protoberberines (8a) and (8b), respectively. This procedure was successfully applied to the synthesis of both enantiomers of xylopinine and bharatamine.

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Reference£º
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem