Total Synthesis of the Marine Natural Product Solomonamide B Necessitates Stereochemical Revision

• DOI: 10.1021/acs.orglett.6b01395
• Publication Date: 2016-06-22T21:08:13Z
• Authors: K. Kashinath; Gorakhnath R. Jachak; Paresh R. Athawale; Udaya Kiran Marelli; Rajesh G. Gonnade; D. Srinivasa Reddy
• Keywords: Natural product; Wacker process

The first total synthesis of the proposed structure solomonamide B has been achieved. However, 1H and 13C NMR spectral data synthesized compound was not exactly matching with that natural B. This prompted us to revise originally structure, in particular, stereochemistry nonpeptide part, which confirmed by its synthesis. During course synthesis, we have developed an interesting hydroxy group directed Wacker oxidation internal olefins a macrocyclic setting.