A Practical and Efficient Asymmetric Synthesis of the Tobacco Natural Alkaloids (S)-Anatabine and (S)-Anabasine via an Allylation/Metathesis-based Approach

Key Points

• The research aims to develop an efficient synthesis method for the natural alkaloids (S)-anatabine and (S)-anabasine.
• Indium-mediated addition of allyl bromide to N-tert-butylsulfinyl aldimines
• Highly diastereoselective reactions
• Ring-closing metathesis to form cyclic structures
• Mild removal of the chiral auxiliary
• High yields of (S)-anatabine and (S)-anabasine were achieved
• Enantiomerically pure products were obtained through the described synthesis method
• The approach demonstrated effective diastereoselectivity in the addition step