Absolute Configuration of Stizolicin and Synthesis and Biological Activity of Its Amino Derivatives

Reaction of the germacranolide stizolicin with secondary amines formed normal products of a Michael reaction at the exomethylene group and simultaneously led to solvolysis with cleavage of the acyl group. The structures of the molecules were established by XSA. Use of the HI salt of one of the resulting amines enabled the proof of its absolute configuration and that of the starting stizolicin, which had previously only been proposed. Stizolicin and the synthesized compounds were screened for antimicrobial and antitrichomonal activity.