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- Title
Asymmetric Synthesis of Crispine A: Constructing Tetrahydroisoquinoline Scaffolds Using Pummerer Cyclizations.
- Authors
Rotte, Sateesh Chandra Kumar; Chittiboyina, Amar G.; Khan, Ikhlas A.
- 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.
- Subjects
ASYMMETRIC synthesis; TETRAHYDROISOQUINOLINES; PUMMERER rearrangement; RING formation (Chemistry); ENANTIOMERS
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 28, p6355
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201300748