Total synthesis of putative montamine and a proposed structural reassignment

Abstract

The natural product montamine was originally assigned as a homodimer of moschamine linked by a N–N′ bond at the serotonin side-chain. A total synthesis of the reported structure has shown this to be incorrect. Analysis of the spectroscopic data suggests that the dimerization site has been incorrectly assigned, and montamine is likely to be a 4,4′-bismoschamine natural product previously described in the literature.