Asymmetric Synthesis of Crispine A: Constructing Tetrahydroisoquinoline Scaffolds Using Pummerer Cyclizations. Issue 28 (12th August 2013) - Rotte, Sateesh Chandra Kumar
Abstract: For the first time, a concise, linear and stereoselective synthesis of both enantiomers of the natural product crispine A has been achieved in six steps with an overall yield of ≥ 20 %, starting from commercially available veratraldehyde. Asymmetric Keck allylation and trifluoroacetic anhydride‐mediated Pummerer cyclization were the key transformations used to construct the tetrahydroisoquinoline core structure. Abstract : For the first time, a concise, linear and stereoselective synthesis of both enantiomers of crispine A has been achieved in six steps with an overall yield of ≥ 20 %, starting from commercially available veratraldehyde.