Total Synthesis and Biological Evaluation of Ipomoeassin F and Its Unnatural 11R-Epimer.

ABSTRACT: Ipomoeassin F, a macrolide glycoresin containing an embedded disaccharide, possesses potent in vitro antitumor activity with an unknown mechanism of function. It inhibits tumor cell growth with single-digit nanomolar IC50 values, superior to many clinical chemotherapeutic drugs. To facilitate translation of its bioactivity into protein function for drug development, we report here a new synthesis for the gram-scale production of ipomoeassin F (3.8% over 17 linear steps) from commercially available starting materials. The conformation-controlled subtle reactivity differences of the hydroxyl groups in carbohydrates were utilized to quickly construct the disaccharide core, which, along with judicial selection of protecting groups, made the current synthesis very efficient. The same strategy w

SUBMITTER: Zong G 

PROVIDER: S-EPMC4651627 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature