Asymmetric synthesis of (1S,2R)-2-aminocyclooctanecarboxylic acid

Article abstract of DOI:10.1016/j.tetasy.2008.12.018

A highly efficient asymmetric synthesis of (1S,2R)-2-aminocyclooctanecarboxylic acid has been completed. This asymmetric synthesis using cycloocta-1,5-diene as the starting material is achieved in 77% yield via a four-step sequence from tert-butyl cycloocta-1,7-dienecarboxylate 10 where the extra double bond adjacent to the unsaturated ester is essential to improve the yield. Furthermore, the Michael adduct intermediate (1S,2R,αR)-14 could be used towards the synthesis of the natural product tashiromine.