Construction of Polypropionate Fragments in Natural Product Synthesis

Abstract

Polypropionates constitute an important class of natural products that possess significant and practically applicable biological activities. Many polypropionates or their semisynthetic congeners are known as antibiotics and as anticancer and antiparasitic agents. Asymmetric synthesis of polypropionates can be designed in terms of stereo‐n‐ads. The most prominent transformations in the synthesis of polypropionate fragments are aldol reactions, crotylations, additions of allenylmetals, and cycloadditions. This chapter deals with the aforementioned enantioselective and diastereoselective transformations leading to polypropionate fragments and polypropionate natural products. Discussions on recent asymmetric total synthesis of zincophorin methyl ester and discodermolide showcase the continuous development of the field. It is demonstrated that the available methods are applicable on a large scale. They have found use in the pharmaceutical industry, which has produced complex biologically active polypropionate natural productsviachemical synthesis in the scale necessary for clinical trials.