Asymmetric Synthesis of Crispine A: Constructing Tetrahydroisoquinoline Scaffolds Using Pummerer Cyclizations. Issue 28 (12th August 2013)

• Record Type: Journal Article
• Authors: Rotte, Sateesh Chandra Kumar; Chittiboyina, Amar G.; Khan, Ikhlas A.
• Is Part Of: European journal of organic chemistry. Issue 28(2013)
• Page Start: 6355
• Page End: 6360
• Publication Date: 2013-08-12
• Subjects: Asymmetric synthesis -- Natural products -- Alkaloids -- Allylation -- Cycli­zation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300748
• Languages: English
• ISSNs: 1434-193X

Abstract

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.