Synthesis of Spongidine A and D and Petrosaspongiolide L Methyl Ester Using Pyridine C–H Functionalization

• DOI: 10.1021/acs.orglett.9b04315
• Publication Date: 2019-12-26T17:48:42Z
• Authors: Florian Bartels; Manuela Weber; Mathias Christmann
• Keywords: Molecular Structure; Pyridines; Stereoisomerism; Oleanolic Acid; 01 natural sciences; 0104 chemical sciences

An efficient strategy for the synthesis of the potent phospholipase A2 inhibitors spongidine A and D is presented. The tetracyclic core of the natural products was assembled via an intramolecular hydrogen atom transfer‐initiated Minisci reaction. A divergent late‐stage functionalization of the tetracyclic ring system was also used to achieve a concise synthesis of petrosaspongiolide L methyl ester.