Last month’s article focused on marinomycin, a cyclic polyketal with rather obvious symmetry – and the synthetic strategy hinged on that feature. However, symmetry in natural products isn’t always so apparent and it is uncovering such ‘hidden symmetry’ that forms the core of this month’s column.
Again, we’re plunging into the marine depths to find natural products with prodigious biological activity. The amphidinolide family comprises over 30 members, varying in architecture but (almost) all featuring a complex and highly decorated macrolactone ring at the core. Amphidinolide F was first isolated in 1991, but as yet remains unconquered territory in synthetic laboratories.1,2However, new ground has been broken by a pair of chemists from Oregon State University, US, led by Rich Carter.3 Their key insight was that hidden symmetry exists in the complex tetrahydrofuran (THF) regions. Although these two regions are not identical, the team considered that enough chemistry was in common that a mutual precursor might be used.