Studies Directed Toward the Total Synthesis of Nannocystin A

Abstract

AbstractA full account of our efforts directed toward the stereoselective total synthesis of nannocystin A, a macrocyclic myxobacterial metabolite, is presented. In this endeavor, we have attempted two distinct synthetic routes to access polyketide fragment (C1‐C11) of macrocyclic depsipeptide (21‐membered) natural product from readily accessible building blocks 1,3‐propanediol and benzaldehyde employing Evans aldol, CBS reduction, Heck cross‐coupling, and Sharpless asymmetric epoxidation as key transformations. Ultimately, accomplished the synthesis of the complete skeleton (21‐membered precursor for macrocyclic depsipeptide) of the nannocystin A possessing desired stereochemistry and functional groups.