Expedient Synthesis of (+)-Lycopalhine A

Williams, Benjamin M. and Trauner, Dirk (2016): Expedient Synthesis of (+)-Lycopalhine A. In: Angewandte Chemie-international Edition, Vol. 55, No. 6: pp. 2191-2194

Abstract

Two amino acids play a key role in the first total synthesis of lycopalhineA. 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.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1433-7851
• Language: English