Expedient Synthesis of (+)-Lycopalhine A.
- Resource Type
- Article
- Authors
- Williams, Benjamin M.; Trauner, Dirk
- Source
- Angewandte Chemie. 2/5/2016, Vol. 128 Issue 6, p2231-2234. 4p.
- Subject
- *AMINO acids
*GLUTAMIC acid
*ENANTIOSELECTIVE catalysis
*PROLINE
*RING formation (Chemistry)
*MANNICH bases
*PYRROLIDINE
- Language
- ISSN
- 0044-8249
Two amino acids play a key role in the first total synthesis of lycopalhine A. l-glutamic acid serves as a convenient chiral starting material for the 13-step synthesis, and l-proline promotes an unusual 5- endo-trig Mannich cyclization that generates the central pyrrolidine ring of the Lycopodium alkaloid. The bicyclo[3.3.0]octanol moiety of the molecule is formed through an intramolecular aldol addition that may occur spontaneously in nature. [ABSTRACT FROM AUTHOR]