Stereoselective Synthesis of Key Skeleton of Mohangic Acids A-E

The key skeleton that could allow to access structurally intriguing mohangic acids A-E has been synthesized in stereoselective manner. The salient features of this synthesis include Evans syn-aldol reaction to construct the C-11 and C-12 centers, HWE olefination to construct C14-C15 bond, Evans asymmetric methylation to install C-14 center and Crimmins acetate aldol to generate C-15 center whereas Wittig and Takai olefinations to prepare the C8-C9 & C6-C7 alkenes, respectively, and Heck reaction to couple C1-C5 & C6-C17 segments of the molecules. The developed route is highly modular and useful for accessing diverse natural product like molecules for future investigations. A flexible route for the stereoselective synthesis of the key skeleton of mohangic acids A-E has been developed. Notably, intermolecular Heck coupling has been introduced to couple an unactivated alkene with an iodo-diene counterpart to install the required triene system of the molecules. The developed strategy is highly modular. image