Manzamine A

Marine sponges are a rich source of diverse and complex small molecules. One such molecule, first isolated in 1986 is manzamine A, which has a broad biological activity profile. In addition, manzamine A has a unique, three-dimensional structure; originally dubbed ‘the molecule from mars’ making it a highly sought-after target for chemical synthesis.

In the biweekly problem session, we have been studying the synthesis of manzamine A which was published in 2012 https://pubs.acs.org/doi/10.1021/ja308826x

We learned about the nitro group, how it can be installed, utilised in crucial carbon-carbon bond forming reactions and converted into other functional groups. The problem session also highlighted the importance of enol triflates in metal cross coupling chemistry and the use of alkene metathesis to install cis double bonds.