Stereocontrolled Total Synthesis of (-)-Aurisides A and B

摘要

Aurisides A (1) and B (2) are unique marine polyketides isolated in 1996 by Yamada and co-workers from the Japanese sea hare Dolabella auricularia,[1a] an organism that has proved to be a rich source of bioactive secondary metabolites.[2] Initial biological screening of 1 and 2 highlighted significant cytotoxicity, with IC50 values against HeLa S3 cervical cancer cell lines of 0.17 and 1.2 g mL-1, respectively. The aurisides are 14-membered glycosylated macrolides that contain a six-membered hemiacetal ring, an E-trisubstituted enone with an E,E bromodiene side chain appended at C13, and different sugar moieties attached at C5 (Scheme 1).