Stereoselective synthesis of the northern hemisphere of the proposed structure of neaumycin B.

The stereoselective synthesis of the northern hemisphere (C-C) of the purported structure of the extremely potent anticancer natural product neaumycin B has been accomplished. Twelve out of nineteen asymmetry centers have been installed chemically. The key highlights of this synthesis include the Krische iridium catalyzed -diastereoselective carbonyl crotylation, the Crimmins aldol reaction, HWE olefination, CBS reduction, vanadium promoted stereoselective epoxidation, Evans methylation and spiroketalization.

Total Synthesis of Lipopeptide Bacilotetrin C: Discovery of Potent Anticancer Congeners Promoting Autophagy.

A convergent strategy for the first total synthesis of the lipopeptide bacilotetrin C has been developed. The key features of this synthesis include Crimmins acetate aldol, Steglich esterification, and macrolactamization. Twenty-nine variants of the natural product were prepared following a systematic structure-activity relationship study, where some of the designed analogues showed promising cytotoxic effects against multiple human carcinoma cell lines.

Late-Stage Functionalization: Total Synthesis of Beauveamide A and Its Congeners and Their Anticancer Activities.

Asymmetric total synthesis of cyclotetradepsipeptide beauveamide A has been achieved for the first time. A macrolactamization strategy involving two possible sites has been explored to find the most effective route for cyclization. A late-stage functionalization approach has been adopted for easy access of non-natural analogues of beauveamide A for further biological evaluation.

Total synthesis and stereochemical assignment of bipolamide A acetate.

Asymmetric total synthesis of an acetate analogue of the endophytic unstable secondary metabolite bipolamide A has been achieved for the first time adopting a convergent approach. The key feature of this synthesis includes Evans's asymmetric ethylation, Wittig olefination, Takai olefination, stereoselective Grignard addition and intermolecular Heck coupling. This eventually developed a synthetic route of the rarely found branched amine bearing an acyloin moiety.